I ripped my music to MP3 at the highest available quality (least compression) setting a few years ago so I could use a music server (Audiotron then switched to SlimServer). I am thinking of re-ripping everything to a higher quality format like FLAC but I also might want to use an iPOD type device someday. Are there any portables that do FLAC or will I have to maintain two copies of everything if I want to use a portable?
One of the reasons I chose mp3 for my rips was because it's compatible with just about everything and I didn't want to maintain multiple copies of the same tracks. Since hard drives are so cheap now (relative to when I started), I no longer have the storage space argument but it still takes more time to rip multiple versions.
My first mp3 player used smartmedia cards and I was pretty limited in memory. I used to rip two versions (64K mp3s for the player) to fit more in it's memory.
There are portables that will work with formats like FLAC and Ogg Vorbis. You will probably need to move away from the mainstream to find them. Look for players from companies like Cowon. Don't expect to find support from companies like Apple, Creative, etc.
Note that many of these players rate very highly among people who care about such things (features, format support, etc.). You are not necessarily looking at lower-quality players just because the companies aren't as well known.
is a good place to start looking into these other players. Check out www.iaudiophile.net
for information on Cowon players.