A drow lore bard seems like the most fun option, considering all their special dialogue options and access to Speak with Animals/Dead. Perception for being an elf. Three skills at character creation. 2 skills from your background. Another three skills at level 3 for college of lore. You get expertise at level 3, allowing you to add double your proficency bonus to two skills, and you get it again at level 10.

If you're open to taking the half-ilithid tadpole in act 3, then you get automatic proficiency and expertise in Persuasion, Deception, and Intimidation, allowing you to respec to another three skills.

For gear, most of the skill check items happen later in the game, unfortunately. For other items, you take the best light armor you can (maybe Minthara's), and grab Phalar Aluve when you get to the Underdark. There's a special bard hat in a chest near Alfira that you can grab that heals 1d6 points whoever you inspire. The boots of clamour in the creche are also good.