I have an old flash drive (clue: it's 256MB) that occasionally plays up but in a very specific way. It is always recognised at home (was xp, then froyo, now gingerbread) and always ok at the library (xp) but is often not recognised or recognised only on multiple attempts at our internet cafe (several machines, windows 7). I tend to think of this as a Windows 7 issue, but I'm always careful to back up irredeemable data.
External hard drives can be really small, I had one that would slip in an anorak pocket. Anorak, well, parka if you want to be pedantic.
Back in my Windows era I had backup fully sorted. Everything was in My Documents including a folder of downloaded software (I would download to and install from that folder) and backup was simply to copy My Documents into a dated folder on the hard drive. That way I could fully recover my laptop from the original dvd and then copy My Documants back in, complete with all downloaded progs to install. Then a week of Windows self updates and I had a brand-new machine with all my old data.
Hope this helps