So I could FLAC encode all my cd's so I would never have to do that again. I'm wondering if I could live with apple lossless, though, given the situation?
YES! I would stick with FLAC. Apple Lossless is proprietary. FLAC is open sourced, cross platform, free, and no chance for DRM

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I would need to convert the FLAC to something that the 2 portables could play.
Yep, but transcoding on a modern computer is faster than having to rerip CDs. And with FLAC, you have a perfect backup, unlike if you rip to MP3s.
You may want to check out
Rockbox. It is unofficial firmware for several MP3 players (including some iPoos) that can play FLAC files. I've never used it, though, but it is something I will keep in mind when I buy another MP3 player.