Are you still up working on that computer?
I know I'm going against the grain here when I say this, but I've had great luck with stability, versatility, and ease-of-use with the Macintosh running MacOS X and the MacLoggerDX logging program from Dog Park Software. I'm never worried that the machine won't boot, the computer will suddenly be filled with viruses, or stuff that worked last week will suddenly stop working today. I've used this for contesting, too, and have had reasonably good luck with this setup, though there were times on St. John when the software was having a little trouble keeping up with the high QSO rates. MacLoggerDX isn't a contest logger, after all; it is just a general purpose logging program.
With all that said, I am considering the idea that I should have other alternatives available to me. The new Macintosh computers have an Intel chip in them so I could run Windows simultaneously with MacOS X with the help of Parallels. We purchased a Mac mini computer this weekend to help us organize our considerable music CD collection and I'm using this new machine to give Parallels a test drive. I have a legal copy of Windows 95 that I had purchased when I built a machine from scratch many years ago that I could install on the Mac mini as an experiment. I spent most of last night working out the details of getting that to work. I managed to get Windows 95 running but the networking stuff was problematic. First I had driver nightmares and then, once I got over that hurdle, the configuration that should have worked didn't. At this point, though, it was very late and the root cause of the problem was probably fatigue and "pilot error" rather than software. Still, I had convinced myself that this is a good arrangement which gives me both worlds on one machine.
At this point it is my intention to buy the smallest (and cheapest) MacBook and configure it with Parallels and Windows 98. (I just ordered a new copy of Window 98 off eBay for about $40. There are enough improvements between W95 and W98 that it seemed worth it.) Though I had good intentions of using MacLoggerDX for the upcoming CQ WW contests, I might get this new machine and start familiarizing myself with it. Many of the Yankee Clipper Contest Club members use the N1MM Logger so I would probably try that one first in the CQ WW SSB coming up at the end of this month.
Again, I want to be completely familiar with all my equipment before I attempt to use it in a far away place. That means reading the manuals and using the equipment in similar situations if I can. Contest are an excellent training opportunity.
Speaking of contest results, I just looked at the write-up for the results of the CQ WW SSB contest from last year. I placed 8th in the US for QRP ALL BAND behind some other excellent operators. With just 5 watts and a low hanging dipole, I did OK! I had not decided what category to compete in this year, but perhaps a noble goal would be to simply beat my previous year's score. I need to think about this more.