So I would like to create a leader of a secret society that are followers of a goddess of darkness, disguise, trickery, subterfuge and assassins (though not necessarily evil). This group is basically a group that gets things done that need to be done with anonymity. Again, they are not necessarily evil. In fact, they tend to be choosy about their jobs. They typically take jobs where some injustice has happened and needs to be corrected or some information vital to the survival of innocent (though not necessarily good) lives needs to be found. This kind of thing. The kinds of things that need to not be tracked back to those who hired them.
For the leader I would like him to be a venerable elf. Something that would fit well with someone good at stealth and subterfuge and versatile enough to have thrived in this line of work long enough to become venerable. Now he is more of a sensai and interested in training those under him and making sure that his organization, and the will of his goddess continues to be fulfilled.
I would prefer that the character be capable of having a somewhat eastern fantasy theme. I do not think that is difficult as most classes can be refluffed in that way.
While I understand that being venerable comes with more negatives than it does positives I would prefer that some of those positive are actually helpful to him. It would be nice if he came equipped with a way to mitigate some of the negatives effects as well, but that isn't necessary so long as he can still remain somewhat effective.
Rule of cool here is more important than raw effectiveness. However, these are my requirements in a nutshell:
1. Stealthy and a master of subterfuge.
2. Venerable Elf.
3. Versatile and capable of remaining effective in this line of work long enough to have made it to venerable.
4. Capable of being fluffed into an eastern theme.
5. Takes advantage of the positives of being venerable. It would be nice if he were capable of mitigating the downfalls of being venerable.
One idea I had was for a Sanctified Slayer Inquisitor who goes for the one shot one kill type abilities with archery. Archery would help keep him out of melee where he would be a liability. Inquisitors are real team players with their teamwork feats and these would still be highly effective. I really didn't want to go with a full caster but Inquisitors at least have moderate casting potential. They definitely have the right abilities to fit into subterfuge and stealth, especially if he takes the Darkness domain. I could even see taking the Travel domain as a possibility.
Venerable Elf by itself carries a huge decrease in Con. In fact, I would say an outright dangerous decrease. The best way I can figure to keep him safe is to keep him hidden and at range.
It sounds like this guy wants to stay as far from the action as possible, is that correct?
I'd suggest a diviner, whether it be wizard/cleric/whatever else, because assassinations tend to require careful planning and intelligence. If you have him make intelligent use of Planar Binding/Planar Ally to call specific outsiders that can take advantage of the target's weaknesses, all the better.
Also, do you have an approximate character level in mind?
Off the top of my head, I don't have any specific suggestions for class, but if he's the leader of a very successful group, he should have no problems procuring magic items that can mitigate his venerable negatives... like a Belt of Mighty Constitution +6. Heck, there's a Belt of Physical Perfection that grants bonuses to STR, DEX and CON all at once.
Sounds like a bard organization to me and bard fits your requirements perfectly.
A venerable leader is no where near a capable in physical combat as he once was, but he shouldn't be engaging in direct combat anyway. He focuses on information and understanding of human behavior. He knows what you will do before you do, and is able to plan for any contingencies.
With an eastern theme a bard group like this would probably be a 'ninja clan' but bard would be much stronger for spies and information gathers than the ninja class would, although having a few specialized assassins on the payroll wouldn't hurt anything.
RumpinRufus: I'm thinking something around level 14ish. I didn't want to go with a full caster. Most of them are unable to pull off the stealth and subterfuge bits. Mostly due to not having enough skills.
WendyWitch: I was thinking of that, of course. I just didn't want to go overboard on giving him equipment that isn't specialized in what he does. Likely a +Con item by itself would be enough to make him not terrible. If he is an archer then a Con+Dex would be appropriate. Some builds do not need Str to do damage, and I'll be favoring those.
C Overton: A Bard, eh? Any build suggestions?
I hadn't thought of a Summoner. Its not a bad idea, actually. As long as he has ways of making himself hidden he could be having his Eidolon be doing most of the heavy lifting. Interesting.
Dave Justus: Huh, second suggestion for a Bard. I honestly didn't think it would be that positive of a choice. Have any build suggestions for this Bard?
If I go with the Sanctified Slayer I'm thinking that Kirin Style would mesh really well with Studied Target.
He could also go for the Slayer Talent that allows him to use a Death attack. With his high mental stats from being venerable and Studied Target raising his DC as well it would make it fairly hard to resist. In that one attack he could also Vital Strike, Sneak Attack and use his spells to buff that attack. It should be one pretty big hit.
shroudb: I'll have to check those out. How do you think they stack up to Sanctified Slayer?
shroudb: Well, you are correct that they do not get advanced talents. I hadn't noticed that. It is unfortunate.
I do not like the Vanguard at all. If it could share the teamwork feats the same way an Inquisitor could then that might be enough to sway my opinion but as written it comes across as severely lacking.
The Stygian Slayer has promise. If the character were younger then I think that may actually be more effective than the Sanctified Slayer Inquisitor.
A Sensai/Bard mix seems interesting but I'm not sure how to build that to fit with this concept. Perhaps I'm missing something?
The Summoner concept I find interesting as well. I typically dislike Summoners as they are kind of the "I can do everything better than you" class. But the concept of this particular build with the character actually being the Eidolon interests me. I'll have to look more into this to see if an Eidolon is capable of filling this role.