One suggestion I would have is to play a Charlatan Rogue and pumping bluff and diplomacy as much as possible. If you wanted you could go Human and take the alternative racial trait "Silver Tongued" which not only amps your Diplomacy and Bluff by +2, but makes it so that if you are successful with Diplomacy they will become more friendly than they normally would.
The charlatan archetype offers the ability to lie to one person and for it to spread over time throughout a city / town.
As for battle, I would suggest that you go the dervish dance build. Helps with defense and you can deal decent damage as well, especially if you're flanking as a rogue.
Or alternatively you could try to use the Betrayer feat as much as possible. Talking up people then surprise attacking them with a knife or whatever you want.
Also, for extra fun, you could go the eldritch heritage feat, which would require skill focus in knowledge in this case, probably royalty from what you're talking about. You can then get a familiar through the Arcane bloodline thanks to the first arcane bloodline power. Then, you could choose something that would give a bonus to bluff or diplomacy. In your case I would suggest the viper, giving a plus to bluff and something that feels evil-like.
In the end though, as a rogue, you can deal damage, especially if you flank or sneak. So I would suggest a rogue over all in this scenario, even though Sorcerer and Witch do give you the almighty magics.
Anyways, that's my 2 cents.
Inquisitors are completely nutters for this kind of stuff. If you take the Heresy Inquisition on top of the Infiltrator archetype, you use wisdom instead of charisma for the Bluff and Intimidate skills, then you add wisdom overtop of the normal modifiers to Bluff and Diplomacy, netting you twice your wisdom modifier to bluff checks.
At 4th level, (wisdom mod) times per day you can roll twice and take the more favourable result on bluff, diplomacy, and stealth checks; which synergises awesomely with the "Escape" Judgement you gain as an Infiltrator:
Escape (Su): Each time the inquisitor using this judgment hits an opponent with a melee or ranged attack, she can use a move action attempt to create a diversion to hide (see the Stealth skill).
Then, as an Inquisitor, you'll get their Bane power and some teamwork feats you can selfishly use for yourself to help you hit and do damage.
Added bonus: because you're getting the above totes nutters bonus to your bluff (by which I mean: twice an ability score you're using for class abilities anyway) as a class ability and not from feats, you can either stack it with feats for more totes nutters bluff, OR take combat related feats and still be a crazy sneaky mofo.
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Oh yeah, Inquisitor rocks this.
Another Option is the Infiltrator Inquisitor, with the Conversion Inquisition. This will gives x2 wisdom on bluff and diplomacy, you will be able cast spells of any alignment, can have a 24/7 misdirection spell going, and gains big bonuses against detect spells.
If you plan to do most things solo, stacking Preacher archetype as well may be good.
Tengu, with the Long-Nose Form feat works for this.
Oni-Spawn Tiefling works well, especially with the Fiendish Facade feat.
I would actually tend to agree with the others that the Inquisitor might be what you're looking for here. They do get some massive bonuses to Bluff, Diplomacy and other such things, but you will be looking at a character focused more on Wisdom than Charisma. So, you may sacrifice a bit of bonus to Disguise do to needing less Charisma, you will most likely have an exceptional bonus to Diplomacy and Bluff not to mention be even better at things like perception or sense motive though. So overall it would be worth it.
As for your questions I'll help where I can (if I can).
If you go rogue, the Master Spy doesn't seem all that bad especially if it fits the character you want to play. You will be missing out on some advanced rogue talents, but the good ones are few and far between IMO.
I don't see why Gregarious and Natural Born Liar wouldn't work together. Natural Born Liar says it doesn't stack with itself and since Gregarious isn't Natural Born Liar, I think you'd be safe.
Personally I don't think Bandit mixes all that well with Charlatan, although there have been some builds that utilize Bandit's second ability quite well for a knock out artist.
The feat seems ok. For disguise self you'd be better off with the Hat of Disguise and having to take the feat 5 times seems like it could be a bit steep depending on if you want to do other things. However, invisibility twice per day does sound enticing. As for the magic wand as a folding fan, that would be up to your DM to allow or work with I would think.
I don't think Ki Pool is worth it unless you intend to dip into Ninja or Monk. Perhaps if you get a Ninja trick from Rogue it could be useful, but I still don't think it's worth it without a dip into Ninja or Monk.
Anyways, as the others suggested, I'd seriously look into Inquisitor (the conversion-infiltrator suggested above) and grab a hat of disguise then you'd most likely be a powerhouse at Diplomacy, Bluff and with the hat pretty good at disguise.
Whatever you pick, make sure it fits the character you really want to play in the end and have fun. Good luck.
Ki pool is good if you're multiclassing Inquisitor and Rogue because, as an Inquisitor, you'd have a high wisdom score on the character already.
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As a side benefit of being a wisdom based manipulator, your Perception and Sense Motive will be quite high. You Will saves will be good too.
This means you are not easily fooled, and you are resistant to effects to delve into your mind.
Of the race choices you noted, human and half-orc are the best choices.