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My character is a halfling rogue lv5 and going to multiclass as a PrC assassin. I've gone over it with my DM and most likely going to level up next campaign, so he has some content written (involving an Oblivion Dark Brotherhood-type guild).

I'm planning on targeting the most challenging foe, then using a lot of hiding/turning invisible, dealing quick and powerful bursts of damage, then running away before other enemies can attack me; basically, a stealth glass cannon with some tricks up my sleeve. Here's my build so far:


Ability Scores
STR: 12
DEX: 20
CON: 14
INT: 16
WIS: 16
CHA: 6

What abilities should I prioritize?

Some skills
Bluff: 2
Disguise: 5 (I have a Hat of Disguise)
Escape Artist: 5
Hide: 18
Move Silently: 15
Sleight of Hand: 9
Tumble: 10

What other skills would be useful? (I have about 1-5 for all my other skills, some of them around 10, like appraise and survival)

Feats
Combat Expertise
Point Blank Shot

What other feats should I get?(I'm planning on getting weapon finesse and death attack from afar)

Weapons
composite shortbow
dagger of venom: poisons target (attacker's choice)
hand crossbow (just cause they can be hidden)
sap

What other weapons are good for assassins? I'm hoping to eventually get some sort of enhanced arrows that can do poison damage or something.

Spells I Want
True Strike
Invisibility/Greater Invisibility
Pass Without Trace
Sleep/Deep Slumber
Darkness
Clairaudience/Clairvoyence
Dimension Door

Do assassins use spells that much? My DM said they weren't that useful...
So, is this a good build for a halfling rogue assassin? Is there anything I'm overlooking, or anything I should focus so much on? Any advice would be great.

Also, if my character's personality/goals matter at all, I'm currently TN (will become CN when I kill somebody for no other reason than to join the assassins; DM said I didn't have to be evil because he wouldn't let us be evil in the first place), my god is Olidammara, and I eventually want to start my own guild of CN/TN assassins. Either that or turn super evil in the endgame and my party has to kill me.

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closed as primarily opinion-based by GMJoe, Miniman, Tritium21, Wibbs, Ruut Jun 10 '15 at 6:42

Many good questions generate some degree of opinion based on expert experience, but answers to this question will tend to be almost entirely based on opinions, rather than facts, references, or specific expertise. If this question can be reworded to fit the rules in the help center, please edit the question.

  • \$\begingroup\$ Assassin spells are situationally useful. You'll want to loom over the individual spells. Nice spread on the stats. Personally I go more into simply for the bonus to death attack and skills but 16 to 18 is good. No less. For tricks you might consider the craft trap making skill and get yourself a copy of the DMG so you can see how traps are built. Can build them yourself and put them out. Also the races of the dragon book has some foldable traps you can carry around with you as a magic item. \$\endgroup\$ – Zakier Jul 17 '15 at 22:00