This certainly sounds like a fun adventure.
Race:I'd suggest hume
Server: if you decide on Phoenix, drop me a line, I have a LS that I'm sure would offer a great deal of help
Job: An idea popped into my head... what about trying to follow, in some vague way, the Final Fantasy Tactics jobs flow chart:
since you are trying to, I think, chronicle your character's "growth". Yeah, an easy thing for me to suggest and not have to do. The melee side translates pretty well into FFXI, the mage side not quite as well, but with a little tweaking could.
Or, just play dragoon.