Optimizing a suboptimal character.

[TLibben]

Hi.

First time trying this so here goes.

I currently have a DM who is just railroading me in an ongoing campaign. My first character has been railroaded so much that I have for a long time felt like he is no longer my character, it's more like playing some guy in the story the DM is telling.

So I've been given permission to make a new character. I was happy. For about two seconds before the railroading began anew. Losing 15200 xp and two levels (from 8th to 6th), as well as having very littel say in the background and motivations of my new character (not that I had that much say with my former character either...).

Stuck between the choice of quitting og getting revenge, I have opted for revenge.

I am stuck with a few non-optional choices. System is D&D 3.5, race is tibbit and class is ninja (CAd version), level is 6, flaws and traits are allowed (2 of each).

Ability roll numbers are 17, 14, 14, 14, 10, and 8.

I need to optimize the **** out of my female gypsy cat-halfling ninja. Any input, bar changing race, class and scores, are more than just welcome, they are sorely needed.

The DM is not that perceptive ruleswise so I have a lot of freedom, though straying from the path of the ninja is the one thing I can not do, apart from a dip or two and prestiges. Alignement is restricted to any non-evil. All 3.5 books are allowed, incl. third party publishers so long as they are 3.5 legal (d20 might fly, but not sure), dragon magazines are allowed as well as online articles by wotc.

My reason for not quitting the group is the other players want me to stay. As well as me being the groups regular DM who had to take a break for personal reasons.

Any help would be appreciated.

[ExLibrisMortis]

You'll probably want to multiclass/prestige out of there ASAP. Going straight swordsage would be preferred at this point, if you want to stay a ninja. Tornado Throw is always fun on a tibbit.

If you want to catch up on power, dip a class with good fort/will and go into Ur-Priest after that. You'll still get 9ths at level 16, ahead of your standard cleric. Wisdom synergy too, technically, though the ninja levels are just filler at that point.

Something like ninja 6/cleric 1/ur-priest 2/bone knight 10 would be quite powerful, even if it's mostly a cleric/bone knight at that point, just technically using different classes. You can also go Sacred Fist (allows you to keep Wis to AC), for that monk flavour.

Note: the second level of ur-priest grants rebuke undead, which may stack with the cleric ability (in which case it may not be worth taking ur-priest 2, as your turning will be sub-par regardless), or it may grant a separate turning pool (which is great for DMM and devotion feats).

[nedz]

Ur Priest has this requirement: Special: The character must have no ability to cast divine spells. So, the Cleric entry is a little tricky.

Ninja is not a good choice of class - casters are much better at redirecting railroads - but there is a handbook here (http://www.minmaxboards.com/index.php?topic=2823) which may help.

[ExLibrisMortis]

It goes on to say you can give up previous divine casting ability to enter Ur-Priest. There's no problem there, you keep turning and domains, and armour proficiencies.

[nedz]

It goes on to say you can give up previous divine casting ability to enter Ur-Priest. There's no problem there, you keep turning and domains, and armour proficiencies.
No it doesn't.

It says "If such spellcasting ability was previously possessed (as with an ex-cleric)" — which kind of relies on a compliment DM — which doesn't seem to be the case here ?

Basically you are suggesting he takes a level of Cleric, "falls", and then enters Ur-Priest. It's the second stage which is the problem since the DM could take any kind of action here.

[Troacctid]

Ninja 1/Beguiler 4/Unseen Seer X. You're still a ninja, DM can't complain.

[torrasque666]

Ninja 1/Beguiler 4/Unseen Seer X. You're still a ninja, DM can't complain.
At that point the Ninja is the dip, rather than the main.

[Vizzerdrix]

Why are you two even talking about Ur Priest? OP said he was stuck in ninja. :smallconfused: I should pay more attention when I read. Sorry. :smallredface:

I'm not familiar with tibbit enough, but maybe a khopesh of the Loyal Minion, or a Sickle of Talons (Both from A&EG) could prove useful.

[Troacctid]

At that point the Ninja is the dip, rather than the main.

Still a ninja.

[torrasque666]

Still a ninja.
True, but the OP specified that he can't leave ninja save for dips and prestige classes. Beguiler 4 and then directly into a Prestige that mainly benefits the Beguiler is pretty much the exact opposite of a dip.

[daremetoidareyo]

So you're locked into tibbit ninja 6.

You got sudden strike and ghost step and wis to AC. Plus a decent bit for skills.


At level 7, consider a 1 level dip of shapeshifter from oriental adventures to get wildshape 3/day. Now you can turn into anything and go can go a warshaper master of many forms route. There is much more utility there.


If you really want revenge, take sacred vow and vow of poverty, refuse to ever leave cat form, Put that 17 in wisdom and take the intuitive attack feat. Now you are a cat that is impossible to hit who cannot be given any gear. Take one more level of ninja to get 4d6 sudden strike, and then switch to warlock. Be a divine invisible cat that coughs up eldritch hairballs. Take trickery devotion cuz its fun.
This route also offers the advanced casting possibilities of going for an apostle of peace. Your fellow pcs are gonna be handing you to bad guys so that they pet you and calm down. "PET THIS KITTEN!"

[nedz]

Ninja 1/Beguiler 4/Unseen Seer X. You're still a ninja, DM can't complain.

Nice build

Ninja 4 / Beguiler 1 / Unseen Seer X would also work; or anything in between.

Obviously the more levels of Beguiler the OP can get away with the better, but we all know this.

[Troacctid]

True, but the OP specified that he can't leave ninja save for dips and prestige classes. Beguiler 4 and then directly into a Prestige that mainly benefits the Beguiler is pretty much the exact opposite of a dip.

Pssh it's still a ninja. Look at it. Totally ninjesque.

Fine, if that's too many levels of the wrong class, go Ninja 2/Cloistered Cleric 1/Shadowspy 2/Shadowbane Stalker X. That's a one-level dip followed by prestige classes. DM can't argue with that.

[Vizzerdrix]

I'll see if the handbook (http://www.minmaxboards.com/index.php?topic=2823.0) can inspire me.

Wis to AC is nice. And a high Wis means Shapesand is a viable option. Go look it up in Sandstorm. It's an alchemical class feature disguised as a 100 gold item.


Sudden Strike only applies to opponents that are denied their dex to AC. No flanking. You may want the get some marbles to help trigger this. I wonder if they can be enchanted the same way as the jumping caltrops so they keep trying to get underfoot on their own?

You get Poison use. Expanded Psionics has hidden talent. It gives you a power. Take psionic minor creation (The one from the Shaper power list) and use it to always have poison handy.

[Warrnan]

The Ninja class is sadly a tier 5 class that has limited invisibility and a difficult to activate source of precision damage who is Multiple Ability Dependent. They basically took away a Rogue's use magic device skill and gave them a few minor monk abilities and made his sneak attack harder to use. Please please consider rogue instead. It's a core class and your dm should allow it by that merit alone.

Ninja, in my reckoning, is a roleplay concept and not a class. To me a ninja is a stealthy person who assassinates enemies with light weapons, poison, or ranged weapons. With a two level dip in monk, you can be invisible every 3rd round all day as an immediate action. This is an Alternate class feature called invisible fist from exemplars of evil. Use standard hide and move silently to be very stealthy the rest of the time. The monk's first level save bonuses will help too.

This plus one level of rogue is my favorite low level "ninja". I would take more rogue along with the ascetic rogue feat. At level 20 you'd end up with 10d6 sneak attack and 2d10 unarmed damage. Class levels would be monk2/ rogue18. You can get more complex and better versions of this basic build but it is a simple way to be a hardcore ninja.

Use magic device for wands. Slap two wands into wand chambers (100g/weapon from dungeonscape) in your dual wielded short swords. Use these wands for swift and immediate action spells like wraithstrike (weapons become touch attacks). Unarmed strike with your knees and elbows.

Use magic device alone can make you so much stronger.

Also. Staggering strike is a must for anyone who can sneak attack/sudden strike. Cut your enemy's action economy in half of they fail a fort save based on 10+damage dealt (most people will). Force multiple saves with Snap Kick feat and Two weapon fighting feat chain.

I also like to dip fighter 1 with the ACF hit and run for an extra feat and Dex to damage against flatfooted opponents and +2 to initaitive.

[daremetoidareyo]

The reason I suggest exalted is that your DM seems to want to excercise a lot of narrative control. Vow of poverty, peace and nonviolence wrest that control away. I mean, they aren't fun to roleplay for any reason other than spite.

[ExLibrisMortis]

Basically you are suggesting he takes a level of Cleric, "falls", and then enters Ur-Priest.
Yes, that's implied to be the most common entry, actually. This is in the introduction of the class: "A member of any class can become an ur-priest, even - and in fact, especially - an ex-cleric."

Although you are right that you don't keep domains as an ex-cleric, and I got that wrong, so that's my bad. Revised advice:
If your DM allows you to enter Ur-Priest by giving up spellcasting (rather than becoming an ex-cleric), then take the opportunity.
If your DM rules that you keep feats that are domain granted powers, cleric 1 remains viable.
If neither of the above applies, I'd dip monk for the saves (and go into sacred fist), or any other class that grants a couple of useful abilities. Duskblade and ur-priest into dweomerkeeper, for example, with Planar Touchstone (catalogues of enlightment, magic) and/or Arcane Disciple, depending on what your DM requires.

[nedz]

Yes, that's implied to be the most common entry, actually. This is in the introduction of the class: "A member of any class can become an ur-priest, even - and in fact, especially - an ex-cleric."

Although you are right that you don't keep domains as an ex-cleric, and I got that wrong, so that's my bad. Revised advice:
If your DM allows you to enter Ur-Priest by giving up spellcasting (rather than becoming an ex-cleric), then take the opportunity.
If your DM rules that you keep feats that are domain granted powers, cleric 1 remains viable.
If neither of the above applies, I'd dip monk for the saves (and go into sacred fist), or any other class that grants a couple of useful abilities. Duskblade and ur-priest into dweomerkeeper, for example, with Planar Touchstone (catalogues of enlightment, magic) and/or Arcane Disciple, depending on what your DM requires.

Well I think the Ur Priest idea is good, it's just the Cleric entry that could be tricky. Suppose you take a number of actions designed to make your character "fall"; but the DM just keeps letting you off because it fits his narrative ?

Hilarious, but no Ur Priest for you.

Ed:
basically, as I understand it, the premise of this thread is that we have an over controlling DM. Any option which requires DM intervention is therefore very iffy and should be avoided.

[Fearan]

Do a swordsage 2 dip and then follow Shadow Sun Ninja. That's basically all you'll ever need on the path of ninja

[TLibben]

Don't know why I had not thought of swordsage and shadow sun ninja...

I know the DM well enough to know that he won't really understand the build and accept just about anything, unlike spellcasting and ninja which will probably be penalized as soon as i mention it.

Thanks for input. Just keep it coming :smallbiggrin:

[Fearan]

Oh, if you can slip an unarmed swordsage for free Improved Unarmed Strike

[Talionis]

Darkstalker feat to make your hide and invisibility work.

2 Monk/18 Ninja and the Ascetic Stalker feat. You get evasion much earlier and unarmed strikes that work, plus Monk feats and bonus to saves.

Ordinarily, I'd say get Use magic Device as a class skill with a feat like versatile but I'm not sure your DM would let you get access to enough magic mart stuff to make it worth your while.

Ninja can qualify for a lot of stealthy and infiltrator prestige classes Chameleon is strong possibly too strong, Master of Masks is actually very Assassin like with the Assasin Mask, but the utility you get from the other masks can make it fun for you. Ninjas where masks. It does advance casting, but very poorly so I suggest getting into a prestige class before you enter with its own shorter spell progression like, Trapsmith or the Assassin prestige class too.

5 Ninja/1 Assassin/10 Master of Masks/4 Assassin

It's harder to break the game without spells so I'd be inclined to give myself as much flexibility as possible to make it fun. Dipping into Incarnum for all the soulmelds can be fun and three levels of Umbral disciple can be very rewarding and on theme for a Ninja

[ben-zayb]

I recomment dipping Dragonfire Adept or Warlock for the Darkness SLA. Grab the Blend into Shadows feat, and enjoy your free Sudden Strikes 24/7.

Ninja 4 / Beguiler 1 / Warlock 1, and then progressing Sudden Strike and Warlock invoking/EB with Unseen Seer 10, would pretty much be a super sniper.

[Troacctid]

I recomment dipping Dragonfire Adept or Warlock for the Darkness SLA. Grab the Blend into Shadows feat, and enjoy your free Sudden Strikes 24/7.

Ninja 4 / Beguiler 1 / Warlock 1, and then progressing Sudden Strike and Warlock invoking/EB with Unseen Seer 10, would pretty much be a super sniper.

This is not a bad plan. Don't forget you need another feat, At Home in the Deep, to be able to see through the magical darkness, because if the target is concealed by it, your sudden strike won't work.

[nedz]

Warlock is indeed an excellent dip for any Rogue type character. Detect Magic at will, a choice of invocation and a means of delivering Sudden/Sneak attacks as a magical ranged touch attack — the ranges even match up.

[TLibben]

Does Unseen Seer's +1 level of existing arcane spellcasting class apply to the warlock invocations and EB?

I mean, without being a bit to RAW. I'm trying to break the rules without having either the DM or the other players being able to pick the build apart by calling me out on any obvious RAW... misuse(?).

But I'm really beginning to like the whole Idea of a landoctopus hidden in its own inkblot and shoting people with mystical rays. :smallbiggrin:

[nedz]

Yes.

The rules for this are in Complete Arcane.

[Troacctid]

And don't forget you're also a teeny little housecat.

[atemu1234]

Dip, what was it, incarnate, to get full damage in cat form. Sneak around in cat form, and kill your enemies with sneak attacks in cat form.

Also, name your character Sprinkles or something, and have fun with it.

Invest in items to boost you Dex to high hell, and definitely go swordsage if you can. There was a feat, IIRC, that allows you to add Dex to damage.

[TLibben]

Update.

Have been in contact with the DM. Good news. Got bumped up one level to 7, will get a bonus feat rather than getting trapfinding a second time from beguiler and waiting for a decision from the DM as whether or not I can use Kung Fu Genius (feat from Dragon Compendium) for the ninja (int to AC and ki pool basically).

Edit: Wrote this as Kung Fu genius got OK'd.

Can also shift around weapon proficiencies. Culture is persian/middle eastern/gypsy rather than japanese.

Still no narrative control. At all...

But things are looking up.

[atemu1234]

Update.

Have been in contact with the DM. Good news. Got bumped up one level to 7, will get a bonus feat rather than getting trapfinding a second time from beguiler and waiting for a decision from the DM as whether or not I can use Kung Fu Genius (feat from Dragon Compendium) for the ninja (int to AC and ki pool basically).

Edit: Wrote this as Kung Fu genius got OK'd.

Can also shift around weapon proficiencies. Culture is persian/middle eastern/gypsy rather than japanese.

Still no narrative control. At all...

But things are looking up.

Could you play a Rogue/Swordsage then? Ask if you can rebuild with the rules from Player's Handbook II for retraining.

[Troacctid]

Dip, what was it, incarnate, to get full damage in cat form. Sneak around in cat form, and kill your enemies with sneak attacks in cat form.
Soulborn, but there's no need to, since you're not going to be using Strength anyway.


Could you play a Rogue/Swordsage then? Ask if you can rebuild with the rules from Player's Handbook II for retraining.
No, don't, Ninja/Beguiler goes up in value if you can get a bonus feat in place of the extra trapfinding.

[TLibben]

Could you play a Rogue/Swordsage then? Ask if you can rebuild with the rules from Player's Handbook II for retraining.

No retraining with this DM.

Trying not to smile to much about getting 1d6 of extra damage every level of Unseen Seer. Sudden strike on odd levels and Eldritch blast on even levels. Will try to get the Deadeye (dex to dmg with ranged) feat as well as already having Craven.

Thanks for all the help and ideas everyone. My mind was getting nowhere.

Just got to figure out what feats to get, aside from Blend into Shadows, At Home in the Deep and Craven.

[TLibben]

No retraining with this DM.

Trying not to smile to much about getting 1d6 of extra damage every level of Unseen Seer. Sudden strike on odd levels and Eldritch blast on even levels. Will try to get the Deadeye (dex to dmg with ranged) feat as well as already having Craven.

Thanks for all the help and ideas everyone. My mind was getting nowhere.

Just got to figure out what feats to get, aside from Blend into Shadows, At Home in the Deep and Craven.

Also flaws and traits. And shopping.

[Troacctid]

You'll want Darkstalker so you can hide from senses other than sight and hearing. I'm also a fan of Obtain Familiar, as the familiar shares all your skill ranks, which is very useful on a skillmonkey. Also, it could potentially remove the need for At Home in the Deep since the familiar can move your Darkness around so you're in it while your enemy isn't. And later, if you're CG, you can upgrade to a coure eladrin via Celestial Familiar.

Noncombatant is the obvious flaw. Murky-Eyed could work too since it should be unlikely that your target has concealment. (Although make sure you have access to a Wand of Faerie Fire just in case.)

[TLibben]

You'll want Darkstalker so you can hide from senses other than sight and hearing.

You mean like all those cool monsters the DM never uses :smallcool:

Will take it if they ever show up.

The DM is so afraid of power that he nerfed rust monsters by taking away their rust attack early on in the campaign. As well as forgetting that undead have a lot of immunities... No PC had any Sneak Attack at the time.

[TLibben]

Murky-Eyed is a must. Noncombatant... We often meet groups of enemies. My plan was combat reflexes (dex is 20), be invisible or hidden inside my own darkness (basically invisible again) in the middel of a herd of enemies. Blasting or slicing AOO, depending on whether it was my turn or not.

Not sure about either my strategy or noncombatant as a flaw.

[Troacctid]

Hiding in plain sight is a swift action, so you can only do it once per turn. Attacking will reveal your position.

If you use ki to become invisible, it will last the whole round, even if you attack, but of course you'll have a limited number of daily uses.

[TLibben]

Could have sworn I saw a feat somewhere that let you sneak attack someone once without them noticing as long as you were hidden.

Hope I did'nt dream about it. If so, then my dreams are really, really boring...

[atemu1234]

Could have sworn I saw a feat somewhere that let you sneak attack someone once without them noticing as long as you were hidden.

Hope I did'nt dream about it. If so, then my dreams are really, really boring...

Mosquito something. Think it was a skill trick.

[Demidos]

Mosquito Bite, skill trick.

If your DM allows level adjustment buyoff, and you go with the kungfu genius, the phrenic template would be pretty much godly. A large amount of completely maxxed psionic abilities (its not that much reading, no worries), bonuses to int, and the magic in the blood feat to boost EVERY ability to 3/day

[TLibben]

So...

Ninja 4, Beguiler 1, Warlock 1, Unseen Seer 1.

Str: 6, Dex: 20, Con: 14, Int: 14, Wis: 10, Cha: 14.

Feats: Kung Fu Genius, Blend into Shadow, At home in the Deep, Darkstalker, Craven and one more. Thinking Improved initiative or Instinctive Darkness (Darkness SLA as immediate action to get around only one swift action per turn, effectively letting me create Darkness AND hiding in it during my turn)

Flaws: Murky-Eyed and noncombatant (unless I find something even more appropriate, thinking pathetic and really giving a cat's tail about Str. Can use Dex for Jump and Climb in catform)

Traits: Aggressive and Quick.

Still got the shopping to do. 19k of GP, nothing more expensive than 1/4-1/3 of the Starting wealth for that level.
So anything that boosts Dex, Hide and overall stealth.

Will function as the party's sneak and thief.

Have found 1st. level divination spells to add to beguiler's list through Unseen Seers' Advanced Learning. Sniper's shot (if it's within range of range attack, then sudden strike may also apply, Good for Eldritch Spear and Chain).

Not much left to do unsless someone sees a mistake somewhere. They happen...

[Troacctid]

The spell you want with Advanced Learning is probably Hunter's Eye. It gives you extra sneak attack.

Instinctive Darkness doesn't change the action required to hide in plain sight, only the action to cast an actual Darkness. It doesn't matter, though, because immediate actions use your swift action for the next round (or the current round if used during your turn), so it wouldn't do what you want.

How about Nymph's Kiss for extra skill points and a bonus to social skills/UMD? That's always a solid choice, especially for a skillmonkey.

[Eisfalken]

I know this will sound awful, but...

...you may need to consider just quitting.

Look, you already say the DM gives you no narrative control of your character. Just say, "I don't think this campaign is really for me, so I'mma duck out of this one. Ya'll have fun, though." If the DM asks what the problem is, say, "I am totally uninterested in this campaign. I don't want to be a character you have this much control of."

And if you really feel the need to play... get your PC killed. What does it matter to you? It's not even really "your" PC, it's the DM's NPC he is making you play. Just kill it off. Have fun with it! Be comedic! "Hey, what do you think is in the Hole Of Unending Agony? I bet it's gold! Or chocolate! (sticks hand in) OH GODS, IT'S HORRIBLE SUFFERING! HELP ME!"

[GreyBlack]

Hi.

First time trying this so here goes.

I currently have a DM who is just railroading me in an ongoing campaign. My first character has been railroaded so much that I have for a long time felt like he is no longer my character, it's more like playing some guy in the story the DM is telling.

So I've been given permission to make a new character. I was happy. For about two seconds before the railroading began anew. Losing 15200 xp and two levels (from 8th to 6th), as well as having very littel say in the background and motivations of my new character (not that I had that much say with my former character either...).

Stuck between the choice of quitting og getting revenge, I have opted for revenge.

I am stuck with a few non-optional choices. System is D&D 3.5, race is tibbit and class is ninja (CAd version), level is 6, flaws and traits are allowed (2 of each).

Ability roll numbers are 17, 14, 14, 14, 10, and 8.

I need to optimize the **** out of my female gypsy cat-halfling ninja. Any input, bar changing race, class and scores, are more than just welcome, they are sorely needed.

The DM is not that perceptive ruleswise so I have a lot of freedom, though straying from the path of the ninja is the one thing I can not do, apart from a dip or two and prestiges. Alignement is restricted to any non-evil. All 3.5 books are allowed, incl. third party publishers so long as they are 3.5 legal (d20 might fly, but not sure), dragon magazines are allowed as well as online articles by wotc.

My reason for not quitting the group is the other players want me to stay. As well as me being the groups regular DM who had to take a break for personal reasons.

Any help would be appreciated.

Commoner 1/Ninja 2/cleric 5/shadowbane stalker 10/cleric +2. Chicken infested flaw.

[TLibben]

The spell you want with Advanced Learning is probably Hunter's Eye. It gives you extra sneak attack.

Instinctive Darkness doesn't change the action required to hide in plain sight, only the action to cast an actual Darkness. It doesn't matter, though, because immediate actions use your swift action for the next round (or the current round if used during your turn), so it wouldn't do what you want.

How about Nymph's Kiss for extra skill points and a bonus to social skills/UMD? That's always a solid choice, especially for a skillmonkey.

Hunter's eye is a 2nd level spell, as far as I know and understand I can not add it to the warlock, and I only have the single level as beguiler. I could always add it and get a wand, but that would be a weak version. Might as well take the Sniper feat from Book of Roguish Luck (allowed I was told by one of the other players and confirmed by the DM) to add 1d6 to ranged Sneak Attacks/Sudden Strikes.

I remembered about swift and immediate actions using the same time slot during a turn/round and was about to edit my entry, but you beat me to it... :smallamused:

I was going to take UMD. So thinking about Nymph's kiss. Party has a Factotum face as well as social skills almost never being used as the DM wants everyone to be IC when communicating with each other or NPCs. The Factotum also has ridiculous Intimidate. Scared a bulette stiff for my character to coup de grace the same round it emerged from the ground...

The party is lacking a good sneaky, infiltrating, pursepilfering thief. I'm on my way to filling that slot.

[TLibben]

Commoner 1/Ninja 2/cleric 5/shadowbane stalker 10/cleric +2. Chicken infested flaw.

I love the Chicken Infested Flaw :smallbiggrin: So much fun :smallcool:

[ben-zayb]

This is not a bad plan. Don't forget you need another feat, At Home in the Deep, to be able to see through the magical darkness, because if the target is concealed by it, your sudden strike won't work.

Another thing of note is that if the build doesn't care much for other invocations, it can also instead just pick up the Devil's Sight invocation for seeing in normal and magical darkness.

[nedz]

Arcane Disciple is the classic Beguiler feat: more spells known. You would need better Wisdom though.

In terms of least invocations I'd be tempted to go with Leaps and Bounds [+6 bonus on Balance, Jump and Tumble].

Eldritch Glaive is also good, but better for Rogues than Ninjas.

See the Unseen and Spiderwalk are good, but Beguiler spells covers half of each of those.

Baleful Utterance is good for breaking and entering, especially when you get Zone of Silence.

[TheCorsairMalac]

I know you asked for powergaming advice, but if the goal of vengeance is to make the DM suffer, I suggest you do as much as you can to make him work, particularly out of session.

A few things that make a DM's job tougher:
Complex rules that make him share his books.(Summoning without the monster manual, applied templates, prestige classes in the DMG.)
Complex abilities that he has to look up to verify if you're right.(Grapple, tactical feats, obscure weapons and enchantments, Alternate class features.)
Frequent trivial battles that require him to draw a map or dig out figures.(Pick fights with people.)
Forcing groups of monsters to make lots of saves.(More dice rolls, more bookkeeping.)
Haggling on prices over everything.(More pointless math.)
Using spells wrong.(Requires reading to verify.)
Splitting the party repeatedly.(More drawing, more imaginative thinking. Make it really bad by splitting up until he draws two encounters then running away.)
Excessive roleplay(gather information in the square, now at the bar, now at the temple, did I mention the docks? Pick a fight while you're there.)
Ask for prices for custom magic items.(Math!)
Sow chaos.(Make him have to think to figure out how his world reacts to your actions.)
Intentionally ignore plot hooks, seeking other work. (Essentially throw away his prepared material for the day.)
Dig into the backstory of every quest giver.(Lots of imaginative thinking.)
Ask for a cool description of every location.(Again, imaginative thinking.)
Wait until your turn to choose what to do.(That wonderful waiting game.)
Always go to the bathroom just before your turn.(Waiting.)

Granted, these will make you a very unlikable player... but they ARE effective ways to mess with the DM(and other players.) I don't recommend actually doing these, but if you're angry enough sometime, they'll probably do the trick.