General :: Syncing Music Across Multiple Platforms?

I recently switched to a Galaxy S3 after owning an Iphone 3GS for a few years. For me, playing music is one of the most important aspects of a smart phone, and I have somewhat specific requirements. I'm trying to figure out the best way to do this:

1. I have a large library of ripped and carefully tagged MP3s on my home PC.
2. I want to add to this library and keep it synced with my phone.
3. I want my phone to be my primary music player. As such, I want to:
3a. Play a song in the car, via the phone
3b. Arrive at work, plug my phone into my PC via USB or connect over the WiFi, and continue to play the same song, sourced from the phone, but output to my PC headphones

What I DON'T want to do is:

- plug headphones directly into my phone while at work
- use the phone interface to choose/play/stop music while at work

That seems simple enough, but so far I haven't found any software that will cooperate.

- "Google Play Music" won't track what was playing on my phone and then update it when I'm on my PC, the two are totally independent. I'm also not ready to totally commit to the cloud, as I have bandwidth limitations and spotty data reception when I'm not at home or work.

- Kies won't properly sort the music on my phone when the phone is connected, nor does it provide an easy interface for viewing or playing music from the phone

- Windows Media Player refuses to sort the songs on my phone properly. It has problems identifying artists and will sort albums alphabetically instead of in proper track order. It's possible that there's some tagging difference between every other program I've used and WMP, and maybe I can rectify this by retagging all of my music to work better with WMP, but that seems like an enormous task and I'd like to avoid it if possible.