This alternative requires the user to be operating in OSX, as Windows doesn't support Apple Lossless(ALAC). But if you own a Mac, using ALAC is mighty helpful. It converts a FLAC-file to ALAC in a matter of seconds, keeps the quality intact and not only that, it also decreases its size to 40-60% of the original size!
ALAC operates on all iPods and iPhones models, so yes, that way would be his first step towards an audiophile addiction.
As for conversion, there a few apps that will do the conversion, FooBar2000 being just 1. There may be better apps available, I'm not a big ALAC user myself, but it's definitely compatible w/Windows.