I’m not sure what happened to the old Redmond widget theme, which was essentially a transplant of the Windows 9X widget style, but if you’re not picky, the .Net theme in the tdeartwork package will probably be Good Enough (or you could go for the different-but-equally-retro CDE/Motif experience). TDE itself, as KDE3, was originally expected to run on an average PC made 20+ years ago—I ran it for years on a single-core Athlon64 with 1GB RAM (and those were pretty good specs for a machine of that era). I don’t know what else Q4OS might be carrying along with it, though.

If you want to go even lighter, look for something offering Fluxbox or Openbox as the GUI—they have enough stuff in them to be useful launchers out of the box, but don’t have the overhead of the true DEs (configuring them may require you to mess around in text files, but you only have to do it once).

Anyway, your main issue is going to be getting any modern browser to work on a machine that constrained. (If your interest is only in looking at Wikipedia, Konqueror, which ships with TDE, can be made to mostly work if you force the use of Wikipedia’s “vector” skin, but the current default skin breaks search and looks like ass. Konqueror’s browser code is way out of date and not recommended for general Internet use.)

Sort of? In my experience, the people working on WINE have always been more interested in game compatibility. Sometimes other software will work, but it’s a crapshoot.

Gentoo will work if you have the time to work through the install, and stick with provided binaries for large packages (or have a lot of patience with updates).

Gentoo will allow you to update the small set of required system packages and their dependencies separately from everything else (emerge --update system), but doing the reverse would require some pretty heavy micro-management.

There are a lot of command-line tools for text, like grep and sed, that don’t work on binary files. Whether this matters to you depends on your workflow. (I use grep a lot.)

exFAT is a Microsoft creation that (unsurprisingly) doesn’t understand or preserve Linux-style file permissions. Neither did any of the FAT varieties before it. So the permissions on the files when you get them back relate to the mount options you pass to the exFAT drive (in this case, you probably want to set dmask and fmask), or the permissions on the directory it’s mounted to.

If you don’t want to twiddle with mount options, you could reformat the external disks using Linux-native filesystems like ext4, but you’ll lose the ability to mount them on Windows if you do that.

Windows just worked.

Excuse me while I laugh hysterically while remembering the sorts of Windows issues I’ve troubleshot for family or coworkers. The one where the combination of a particular Windows version + a particular MS Office version + document previews being activated would cause Office to crash randomly on operations that had nothing to do with document previews was particularly memorable and difficult to figure out. The various Linux snafus I’ve had to deal with were pretty easy to handle by comparison.