With an 8088 you can run Windows/286, but I think Win 3.1 is out. I'm fairly sure Windows for Workgroups is out, though, as it requires a 386 and Win95 cannot physically run on anything less than a 386; even if it did it'd be abominably slow.
You'll have trouble loading XMS with an 8088 too, as HIMEM.SYS requires an 80x286 CPU...
It is true, though, there is a fair amount of stuff... just this weekend I got my PowerPC board in my A500 firing up (using my Reference 40 HDD as a SCSI interface to my Zip drive - it appears to be compatible with the Dataflyer, luckily) and have got Railroad Tycoon running ok... I'm sure Ultima 1-5 and probably 6 will run too, and Civ should be fine....
Oh, Powermonger runs on 286s too, and comes on 5.25" floppies originally, but you can download it these days.
Incidentally, your 2286 will run 1.44MB floppies fine, but if you're going to use it get an ISA SVGA card as CGA won't run anything fun.... (apart from adventure games, of course!)
