Boosting Skill Checks

[FocusWolf413]

I want to crank up my escape artist skill as much as possible for the lolz. Is it possible for me to consistently hit DC80 by level 7? All pathfinder and 3.5 stuff is allowed.

[Deox]

Without trying too hard:

Halfling Factotum 3 / Cleric 3 / Marshal 1

32 point buy
Str: 6 (8, -2 racial)
Dex: 20 (16, +2 item, +2 racial)
Con: 8
Int: 18 (+2 item)
Wis: 12 (11 starting +1 ability at 4th)
Cha: 18 (+2 item)

Traits:
Slippery, Skinny. Both provide a +1 bonus, netting a +2 to escape artist.

Feats:
1st - Skill Focus - Escape Artist
3rd - Abberation Blood - Slimy Skin
6th - Practiced Spellcaster

Items:
+2 cloak of charisma, +2 headband of intelligence, +2 gloves of dex (12,000 gp total)

+10 (ranks)
+2 (traits)
+3 (Skill Focus)
+4 (Abberation Blood - Slimy Skin)
+20 (Guidance of the Avatar)
+12 (Divine Insight)
+5 (Dex)
+4 (Int)
+4 (Cha)
+3 (Cunning Knowledge)
= +67

[FocusWolf413]

Awesome. Thanks. And I can also get skill bonus items and stuff.

[dextercorvia]

If you are an Uur Sigil Illumian, you get +2 to all dex based checks, which beats a Halfling's +2 to Dex (for this purpose).

[Psyren]

If you are an Uur Sigil Illumian, you get +2 to all dex based checks, which beats a Halfling's +2 to Dex (for this purpose).

Wouldn't halflings also get a bonus for being Small? Or does that not apply to escape artist?

[Jeraa]

Wouldn't halflings also get a bonus for being Small? Or does that not apply to escape artist?

Size only gives a bonus/penalty to Hide checks.

[dextercorvia]

Wouldn't halflings also get a bonus for being Small? Or does that not apply to escape artist?

As stated above, there isn't a skill bonus for being small. There is an implicit bonus for most size decreases if you are only using it to squeeze. However, even there, Small and Medium creatures are treated the same since it is based on the size of your space.

[Zaq]

The Acrobat Boots soulmeld gives you +2, and +2 more for each essentia you put in it. By default at level 7, you can invest 2 essentia in it, for a total of +6, though you could make that cap a little higher with 3 levels in Incarnate and/or the Expanded Soulmeld Capacity feat (for a total of +10 if you had both of those). It's an insight bonus, so it'll stack with some things, though not with everything.

It can't compare to the +20 given by Guidance of the Avatar or the +lots given by Divine Insight, but it lasts as long as you want it to, doesn't have a use limit per day, and it doesn't even take an action (aside from the swift action to allocate essentia to it, but that can be taken at any time).

If you're allowed to have friends helping you, there's always Universal Aptitude for an untyped +5, if you can find a friendly Truenamer. Technically you could even do it yourself with just a single level of Truenamer (it's a level 1 LEM utterance, so you can pick it up immediately), if you're willing to keep your Truespeak check up.

[Deadasadoor]

There is a skill trick (Complete Scoundrel) that gives you a bonus based on how large the thing grappling you is. Up to +16 if it's colossal.