i just got the same idea about last week. i cleaned out my room, found my old Wing commander stuff. I found my Kilrathi Saga (tempted to sell that on ebay for 150 and up.. but i can't seem to let go) my wing commander 4 cd set, my privateer cd with RF set and my Privateer 2 cd my Prophecy Gold Cd's. but alas my old flight stick is broken.
i got the kilrathis saga to work.. WC1 and 2 (with sm and so missions downloaded) both of these work fine. Wc3 works but the game isn't recognizing the gamepad i have through the USB port (spent like 3 hours this week searching manhattan, nyc for a old gameport Flightstick.. sucks) WC4 crashes after about a little while with gamepad usb problems, and the video suffers the same fate as Prophecy, stutters. and unlike when i was running the game in 98, i can't get the game to not enable hardware accelaration without the game freezing the movies.
so i'm going back to enjoy the first 2 wing commanders. I'll play 3 and 4 soon hopefully. Privateer i'm starting to give up on playing. I've spent SO much time trying to get it to work. I have installed vmware trying to get my old dos 6.0 to run on my new system. but i can't get the sound card to work and again i have no flightstick that attaches to the gameport. Privateer 2 is almost working. Prophecy is playable but i can't enjoy the movie aspect.
I'm thinking about rebuilding an old computer. i have an old PII 450 mhz (when i first got that i upgraded from an old 585 133mhz proccessor that was upgraded over a 486 DX 33). But i'll have to get a new mobo, case, sound card, HD, memory, etc.. etc.
i'm hoping to rebuild something that can run it. prolly run win 98. hoping to spend under 150.. but i doubt it..