I would not have a library with FLAC and MP3. I find myself constantly updating and modifying tags, and couldn't imagine trying to keep track of changes to two versions of each song.
It would be very time consuming to manage both.
I have family members who uses i tunes/ipod so i normally batch convert the whole library about once a year for her. it takes a full day to convert then half a day to transfer onto her computer.
Im not going to do it anymore. Huge waste of time. It is a lot of work just to support a lame device. I would rather buy her a Sansa fuze+ for $100 that plays flac than do the conversion again(been doing it for 5 years). I suppose the problem is that she won't move on from the ipod. Im not going to be an enabler anymore, so she may have to.
There are some really nice devices coming out right now that should be great alternatives to ipods. Last year didn't have much. There are android devices available from Cowon, Archos, Samsung, and Creative.
They would all sync with J River and support conversions, though Flac should be supported thus making conversion unnecessary.
If you consider the time wasted trying to accommodate an apple device, it makes a lot more sense to spent a bit of money on something else.
You can get an 8GB sansa clip+ that plays flac for $60.
If you are ripping you CD collection, lossless is the only way to go. I ripped my entire collection to mp3 years ago, then re-ripped to flac two years after.
That was another waste of time. Its best just to do it once. Properly.
I recommend to Rip once, and have one library with one version of each track in the most compatible format, FLAC.
Portable devices are irrelevant when it comes to ripping and organizing you music collection. The iphone probably won't work in a couple years, but your FLACs will last forever.
As long as you back them up periodically.