Min/Max Boards

I've been playing 3.x for over a decade and I'm now presented with the opportunity (demand) that I finally play my first caster type.  I've always opted to play melee or archer type characters.

The party I'll be joining consists primarily of new players who have had priority in picking thier roles. (I was nice enough to offer to build my character last to fill any needed gaps in the party).

As it stands the party currently has no skill monkey, ranged, or arcane caster.  Bard was the first direction researched, but haven't really found something that will do what I need...

1. Something that fills as many of the roles as possible.
2. Something optimized to the point that I can cover down on the parties lack of play experience.
3. Something quirky, and fun to roleplay.
4. Something playable at the starting level of 5, that will scale well as we level.

All physical books are allowed so far except for exalted deed, vile darkness, lost empires of faerun, and dragon magazine.

2x flaws are allowed
Trait is allowed

We start at lvl 5 with 9k gold, heavy warhorse, and a military saddle.

Any help would be greatly appreciated.