1) I was planning to use WAV files as the format of choice to play through my main home stereo but I take it that WAV files do not support tags so I am probably going with lossless. I kind of feel that now is the time to make a choice as I do not care to duplicate this work in the future. All Apple (ALAC) or all other...google? (FLAC). When my iPhone dies, I will look hard at an android if there is a good, not too big phone out there. I'm too cheap to dump the phone yet though. Apple seems easier but their our way or the highway 'tude chafes my **s. Any thoughts on this?
I wouldn't use WAV. I'd strongly recommend (as others did above) using a more modern file container format such as FLAC or ALAC.
If you want to use the lossless files
directly on your iPhone, in the built-in Music app, then you have to use ALAC.
I probably would not (actually, I know I would not, because I don't). I'd recommend ripping to FLAC instead, and just transcoding a lossy version of the files for syncing to your phone.
Most places where you use your iPhone are not going to be low-noise environments, first of all. Plus, the lossless files are so much larger, and space on your device is likely going to be limited. So, I'd rip to FLAC and use those at home, plus you can stream them to your device through JRemote if you have a fast enough WAN connection, so even for travel on the road, you can still use them, so long as you have good cellular and decent upstream bandwidth at home.
Then, only for those instances where you need to use stuff on the road where there is no cellular (so, on airplanes, camping in the backwoods, etc) you can sync some high-quality MP3s to your device. I use MP3 -v4 now, though if you're
really concerned about quality, just use MP3 -V0.
There are a few ways to do this, but I just sync my
entire Library (less some tracks I never want to ever put on my phone) to MP3 with MC's built in handheld system. I store these copies in a folder that MC doesn't watch, so it never knows about or sees them. This does cost storage space, but since I use MP3 -V4 it isn't that substantial (around 350GB for ~37k tracks). It stinks to give up that space, but after playing with it a lot, this worked the most reliably with Apple devices and dealing with iTunes.
Then, I import
these into iTunes and use
prod's MCiS to sync between MC and iTunes, and iTunes to sync rotating smartlists to my devices. iTunes never "sees" my "real" files, it only sees these MP3 copies (which also has the benefit that it can't mess them up).
It would probably be best to start a separate thread if you want detailed help with some kind of scheme to do this.