I know amazon lets you download to your phone- you don't always have to be connected and streaming. (Pretty sure Google does as well, but I don't use it.)
It's a great way to sync without the hassle of hooking up with wires.
I'm in the process of uploading all my music to amazon cloud as I'm typing this. I like the idea of zumocast but having to leave my computer on all the time didn't seem like a good idea. I opted for the 20gb for $20 but amazon has a "special" going on that you can upload all the music you want and it doesn't count against your 20gb allotment.
I've read that its incredibly buggy since it is still in beta. I have no problem with 20 bucks a year for unlimited space for music and 20gb for everything else.
I've spent more time than I care to admit trying to figure out this same problem on my own, and just about everything I tried had some kind of issue (e.g., new programs didn't import playlists properly, buggy software, playlists didn't transfer to phone, too many steps, etc.). All I wanted was to sync my music in the same way I could with my iPod, be it through iTunes or some other half-decent program. If you're willing to rebuild your library, playlists, etc., Windows Media Player seems to do the job.
If not, here's something I stumbled across yesterday while browsing the FAQ in the Help app: Motorola Media Link. I've only used it for a day, but I haven't encountered any problems syncing playlists with it. So far, the only thing I can think of to discourage you from it is this: if your library is too big to sync in its entirety, the options for handpicking particular songs are somewhat limited. Of course, you can work around this by just building a playlist with everything you want, but keeping that updated would be a hassle. I have a smaller library (8GB), so it's easy enough for me to just drop everything on there and forget about it, but it's something to consider.
The only other free, non-cloud-based solution I've found to be fairly seamless was MediaMonkey, which imported my playlists without trouble. It's a very good program, but it has a LOT of features that most people, including me, will never use. If you don't mind all the clutter, though, it's worth a look.
Last edited by bushpilotwannabe; 10-03-2011 at 03:55 PM.