There's a good question, and kudos to Mjr. Whoopass for coming up with something fairly original to actually sit down and think about.
During wartime, I'd probably just go from one odd job in some backwater system to another...maybe see about getting a civilian pilot license just so I could come and go as I please...maybe even scrounge up enough money to buy my own rust bucket to fly around in eventually. I'd be curious about the Kilrathi and would want to do my own research on 'em, but I imagine Confed would make most of the important nitty-gritty stuff about 'em classified. Alternatively, I'd probably just be a support guy - communications? - on some unimportant ship that sees limited (or no) action. Like most, I can talk the talk in a video game, but if it came to real life with no reset button, I'm not too keen on fighting a war until it starts fighting me. Might feel differently if my family situation was different and I was an orphan or lower class financially and signing up was the only way to see new places, try new things, get an education, and get paid to do it. But too many extras, side characters, and near main characters get creamed in Wing Commander. Might as well slap one of those red Trek security outfits on me; I'd be screwed!
Post-war, I'd take an interest in studying the Kilrathi (books pertaining to culture, religious persuasions, etc.) just for curiosity's sake. I'd probably move out to the Border Worlds to watch a younger government grow (probably less restrictive in terms of policies - so it might have a greater sense of personal freedom and place more importance on the individual), maybe actually consider serving on a BW capital ship of some sort...maybe land some kind of support job there (engineering?). Alternatively, I'd stand in as a police pilot somewhere to help keep an eye on the borders. Of course when the whole Black Lance thing starts to go down, I may or may not wish to seek alternative employment opportunities...
Flying under the radar is the way to go in the Wing Commander Universe, baby!

I could always win as Blair, but never did it in the first life!
