Well, as for running OP2, I believe it is possible. The best person to ask would be TH300, as he uses Linux for his main system (I'm pretty sure).
I don't think he has gotten much success under WINE.
(I have a linux system of my own, but I don't do any OP2 related development on it, and certainly don't try to play OP2 on it)
As for myself, I have tried running it under WINE on Slackware Linux 9.1 (this was quite a while ago). It did seem to work, however it ran too slow to be unplayable. (I did have a 333mhz PII so that was probably part of the problem).
I don't believe sound worked either. (My sound config was sort of screwed up, I don't think any sound coming from WINE worked at all, even though ALSA worked with other apps fine)
Also, the menu didn't work quite right, but you can get around that by editing Outpost2.ini and setting SpiffyDraw=0. (The menus won't look nice like they are supposed to, but the game will work fine)
Someone else might have gotten it to run under WineX / Cedega (it's by Linspire, you can get its source off of CVS) but I can't remember any details about it.
As for Darwine, results could be better or worse. I don't know if it's based off of the same codebase as WINE (though I would like to think so).
I am assuming that you are running on Mac OS X, correct?
If none of this works, a last option would be to install a whole PC emulator and install windows onto it to play OP2 that way. Bochs, QEMU, plex86 are a few freeware emulators I can think of, VMware is a commercial one (runs on Linux host, I don't know about OS X). I use VMware myself (to run linux on this winxp system I have) and its speed is quite impressive. (Should be good enough for multiplayer if you have a decent system). I think one of our members (I believe it was neutrino) runs OP2 on NetBSD this way (using vmware or something similar).
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Anyway, hope that helps.
Welcome to the community! hopefully see you on IRC sometime!
-- op2hacker