You're very welcome.
.flac files will play through airfoil in itunes--that is what you meant, right?Yes, although I've never tried it and I'm not in a position to do so. It's only something Google told me was possible.
I convert FLAC files to either Apple Lossless or AIFF all the time with XLD and it always retains whatever metadata is present in the original FLACs, including artwork and other song info.
If you were viewing FLACs in iTunes and adding metadata
there, it wasn't being embedded back to the file. iTunes relies on its database structure to present song metadata. So when another app like XLD or whatever picks up the file and converts it, there's no metadata in the file to hang on to. Make sense?