If I could be an innkeeper... I would be a busty/lusty/musty wench type keeping an inn in the lush countryside. I'd be friends with all the adventurers that came through looking for work and I'd give the elves free beer.
I'd have a fine stable of horses that would be available to those on long urgent journeys...they could leave their worn out horse with me and take a nice fresh one. I'd serve hearty soups and roast beast, every night there'd be a qualified Bard singing songs and an open fire keeping everyone toasty.
If I could be a professor... I'd be a professor in Film Making and would hold stuffy lectures about theory and so on. I'd reccommend the Disney Family Movie in 48 Hours to build teamwork in crews.
If I could be a writer... *sighs* Get up 9ish most mornings. Make tea and have breakfast reading through what I wrote yesterday. Write all morning, and break at about 2pm for the day unless deadlines were getting near or I'm on a roll. The rest of the day would be either housework and reading or visiting people or seeing movies or wandering around town.
If I could be a backup dancer... I wouldn't accept any jobs from Hip Hop or Rap artists and I'd keep my clothes on. I'd like to work with Gewn Stefani cause she's cool. If I wasn't a music video dancer but a stage dancer then I'd want to be invloved in modern ballets danced classically, like Dracula and Maui.
If I could be a bonnie pirate... I wouldn't kill people. I'd take their chocolate and candy and brand their ships with my mark so that everyone knows how awesome I am. Cary Elwes would be my valet ;p
After five years marauding I'd retire and live like a King in Patagonia. Or Rarotonga. Or the Greek Islands.