I've played with this quite a bit and described my method and suggestions over here:
http://yabb.jriver.com/interact/index.php?topic=47343.msg326700#msg326700I will say this: It sucks that Apple and Microsoft and everyone seem to want to play their stupid games. I wish they didn't, and/or I wish there were a viable alternative. Perhaps Android will one-day be one, but for now it looks like it might be more of a Windows Mobile killer than a iPod/Zune/iPhone competitor. However, this trend is showing no signs changing in the future. Even when JRiver does "get it" and breaks their way in, they're going to just get locked out again come this time next year.
For a near term (and long term) standby solution, make MC's Generic Handheld system (syncing to a folder on your hard drive) able to fully emulate an iPod/iPhone/Zune/whatever in every way:
1. Stop locking down the Generic Handheld conversion functions. Allow conversion to iPod/iPhone/Zune/whatever compatible video formats when syncing to a folder on a hard drive.
2. Support bookmarking of podcasts and audiobooks on unsupported iPods somehow. If this involves wiping and re-programming the iTunes database every time I sync (in order to use it as an "external sync tool") then so be it. They don't seem to "break" this as often. I have tools on OSX that muck with the database that have worked for many, many versions.
3. Allow us to set a size limit on generic handhelds.
If these three things were done, it would be a HUGE help in allowing us to use our devices while JRiver does get real support figured out. It would also give us confidence that we will have an interim crutch if Apple re-breaks our support again with some future firmware update. The alternative is people considering just bailing on the whole thing and going back to iTunes.