Answering a couple of your added questions:
Yes, the Clip+ has improved firmware over the original Clip. It adds folder navigation, near gapless, ReplayGain capability, current/next track info., and faster screen scrolling, among other things.
Rockbox currently is being worked on for the Clips (and the Fuze). Almost certainly will come to the original Clip first before the Clip+ (and possibly the Fuze before that). It currently will work, in a development build, on the Clip v1 (the first hardware version of the Clip; there are 2 hardware versions), but can freeze up. Hopefully this can be corrected and a finalized version will issue, but there never are “guarantees” with Rockbox and there is no schedule.
If your brother just wants to grab a small player on the run, the refurb. 2gb Clip at $20 may be a good deal. But again, no video with it, and it navigates by ID3 tag, not folder (the Clip+ adds folder navigation), and further firmware revisions for it are unknown.
