- Ritual: Glib Limerick (Roll Twice, take better, statistically a +4) Gained by Feats: Vistani Heritage, Vistani Jongleur
- MC Shaman for the Speak with Spirits daily, giving you your wis mod as a bonus. (This character is going to have such MAD, it's not even funny.)
- Feat: Psionic Skill, +2 feat bonus + (spend 1 PP for a +3 power bonus)
Feat: Disciple of Lore: +1 bonus to trained skills
PP: Traveler's Harlequin if you can swing it, Silver-tongued Scoundrel if you can't
Assuming you go Harlequin, that frees up the vistani feats for bardic ritualist and arcane familiar (serpent, because hey, tradition, or Air Mephit if you retrain it for itself at 11 to upgrade to paragon familiars)
- Feat Armor proficiency Leather for Skald's Armor is worth it
You may want to invest extra feats into your familiar making it a better scout to create more believable lies.
- Item: Shadowdancer's Mask gives you another bluff reroll
- Feat: skill power, Level 10 diplomacy skill power: Befrend
Grab "Faulty Memory (bluff utility 6)" as it's a great way to make sure they don't question your disguise. If your DM isn't using the "one free action per turn" rules, grab "Fast Talk (bluff utility 6) as well"
After this cursory optimizing, assuming Harlequin, you'll have: +5 (cha) +6 half/level +5 trained +4 item (skald's armor) + 3 feat (skill focus) +5 power (befrend) +5 untyped shape of the traveller +2 speak with spirits = +35
Roll twice, use either result, the reroll (either both or the lowest, depending on your GM's interpretation of shadowdancer's mask interactions with glib limerick) We'll call that a rough +6 on the roll, give or take. For an average roll of 51 at level 12. Where a "Hard check" as per latest DCs is a DC 28, and most insights will ... be around +16 or so? You count as the creature's type and keywords (from false-blood) and speak their language, have an invisible scout (Air Mephit) for gotchas, and can sustain (via form of the traveller) past an extended rest and being stripped naked.
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Drow, Psion, Traveler's Harlequin
Discipline Focus: Telepathy Focus
Psionic Skill: Psionic Skill (Bluff)
FINAL ABILITY SCORES
Str 9, Con 12, Dex 13, Int 19, Wis 14, Cha 21.
STARTING ABILITY SCORES
Str 8, Con 11, Dex 10, Int 16, Wis 13, Cha 16.
AC: 25 Fort: 19 Reflex: 23 Will: 25
HP: 68 Surges: 7 Surge Value: 17
Diplomacy +21, Insight +14, Bluff +26, Arcana +16, History +16, Nature +14
Acrobatics +7, Dungeoneering +8, Endurance +7, Heal +8, Intimidate +13, Perception +8, Religion +10, Stealth +9, Streetwise +11, Thievery +7, Athletics +5
Bardic Ritualist: Ritual Caster
Traveler's Harlequin: Spirit Talker
Level 1: Bardic Dilettante
Level 2: Bardic Ritualist
Level 4: Arcane Familiar (retrained to Arcane Familiar at Level 11)
Level 6: Psionic Skill
Level 8: Disciple of Lore
Level 10: Armor Proficiency: Leather
Level 11: Skill Power
Level 12: Skill Focus (Bluff)
Psion utility 10: Befriend
Ritual Book, False Blood Amulet +2, Skald's Drowmesh +3
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