Build advice for a true rogue character

[Matrota]

I'm playing a 3.5e campaign with some friends and I'm nearing a point where I'll be able to prestige, and I wanted y'all's opinion on order of feats and build path. Campaign is somewhat average to low optimization, DM isn't a fan of builds with more than 2 base and prestige classes, thinks they're annoyingly tryhard.

At the moment I'm a 4th level ash elf rogue (dndwiki homebrew race) with the dark template. I have quick draw and weapon finesse, and I typically fight by flanking and abusing hide in plain sight for a bunch of sneak attacks. I also frequently craft my own poisons with the craft skill. Thematically, my character is a very skilled master of stealth, who is a bit of a coward. He never fights alone unless he's guaranteed the victory, and he's much more combat oriented than socially oriented.

My ideas for after this are either going into assassin or shadowblade. Feat-wise, I want to get darkstalker from Lords of Madness, Craven from Champions of Ruin, and Telling Blow from PHB2. What would you giants reccomend? And what order should I prioritize my feats?

[DEMON]

Hello.

What's your current level and your stats?

What feats do you already have?

Do you use the multiclassing penalty?

And what sources do you have available? You're already using a homebrew race, so that might open even more options than the normal "all books allowed" scenario.

[Rebel7284]

Assassin is the better option. Full BAB, sneak attack is better than sudden strike, and it's always good to have spells.

[DEMON]

Assassin is the better option. Full BAB, sneak attack is better than sudden strike, and it's always good to have spells.

Full BAB? Assassin is 3/4.

Also, there's a non-evil variant floating on-line (Avenger), that's actually official.

But my suggestion would actually be either Swashbuckler or Beguiler, if we're limited to only 1 other class on top of the rogue (sorry Unseen Seer and 1-level Fighter dip).

[Matrota]

Hello.

What's your current level and your stats?

What feats do you already have?

Do you use the multiclassing penalty?

And what sources do you have available? You're already using a homebrew race, so that might open even more options than the normal "all books allowed" scenario.

Stats are as follows:
STR: 17
DEX: 20
CON: 16
INT: 17
WIS: 11
CHA: 15

4th level, ECL 5 due to dark template. We do use multiclass penalty, and every official source, including dragon mags are open. DM allowed homebrew race since it was barely a change from normal elves, just gained hide and move silent buffs mostly. I have quick draw and weapon finesse.

[ATHATH]

Hm... Maybe dip into Whirling Frenzy Lion Totem Barbarian so that you can Full-Attack people while they're flatfooted during the surprise round of any given combat? (Trickster) Spellthief might be an option as well; you can "steal" (a.k.a. have them voluntarily give) personal-range spells from your party's spellcasters. I think there was a prestige class that can steal spells as well, but I forgot its name. A Sneak Attack Fighter dip can get you some nice weapon and armor proficiencies.

[DEMON]

I think there was a prestige class that can steal spells as well, but I forgot its name. A Sneak Attack Fighter dip can get you some nice weapon and armor proficiencies.

Hellbreaker (FC 2) can steal spell likes. Not sure there's a spell-stealer PrC.

With multiclass penalties and Monk/Ninja as your favorite classes, you're better off with a PrC, I guess (or going with a 9/11 alternating build, but that's no longer possible, unless you want to suck it for the next few levels).

[ATHATH]

Hellbreaker (FC 2) can steal spell likes. Not sure there's a spell-stealer PrC.
Yeah, that was the one that I was thinking of. Thanks.

[Rebel7284]

Oops, it is 3/4ths for Assassin, my bad. The rest of my points remain.

Also, something that is a bit out of the box but can be really good, Telflamar Shadowlord. Perhaps enter with Jaunter.