not to knock the apple lossless scheme or anything, but check out rockbox. You can load it onto most ipods and it sets up as a dual boot.
It allows you play flac and many other types of files, plus it utilizes a (much more user friendly) file tree system as opposed to itunes.
Kind of complicated to install, but easy and very cool after that.
Check it out
http://www.rockbox.org/ (i'm just a happy user)
I also use foobar2000 with live show tagger now (awesome!!!) and have ditched winamp, which always seemed to buggy for me.
Tag&Rename is another great program for organizing your flac tags, it's especially helpful with commercial cddb stuff and also with renaming filesets automatically.
I personally don't mess with anything but wav and flac. I record to wav. I archive with flac.
This is true for all my masters and subsequent mixdowns, plus all 16/44 stuff such as Cd's, Dats, downloads, etc...
It's all just stored on redundant hard drives. One installed in my home machine and one offsite.
I've converted everything to one format. With rockbox/ipod, foobar2000, and a hard drive.....you are all set. No more conversions.
A lot of work, but it works for me. YMMV......
Cheers, Phil