You'd think an IBM operating system on an IBM ThinkPad would be easy-peasy - but good grief, it's taken me over a year to finally get a magic formula that works. Not too new, not too old.... (and yes, I have ArcaOS too, but I wanted an OG 1994 install)
One interesting thing I found is that OS/2 can actually run SecondReality (in full screen, but it suspends it when I ALT-ESC to something else) -- including with SBPro audio. I couldn't do that with WinXP yet (same hardware), even though trying explicit DOS settings. I may tinker some more on that, but rebooting to "MS-DOS Mode" in 95/98 can changing EMM386 from NOEMS to RAM then SR works. I'll do a write up on the adventure soon-ish, I'm still trying to figure out the TCP/IP settings stuff for OS/2. My first experience on the Internet was "borrowing" my sister's credit card and racking up $100 for an afternoon of web-surfing on dial up, with OS/2 Warp in 1994. A graphical Traceroute was so neat to see, a graphical Gopher, and some early web sites. Frankly, that day I fully realized that "BBS's are done for" (or cute ANSI couldn't compete with HTML). I paid my sister back, eventually. At the time I thought it was just an activation gate, didn't realize there was a per-minute charge. Sorry sis! Don't leave your card out on the table :P -Steve