I found what I needed. Sounds like it's perfect for my needs. You install an app on the phone and a client on the PC.
I'll try it out tomorrow and report back if anybody needs similar functionality and wants to know how it works out.
Try Dropbox. The developers are working on an Android app, but there is currently an independently developed app called Droidbox available. I've used Dropbox for about two years and it is great, but I can't really tell you how good Droidbox is. When the Dropbox app comes out, I think it will be exactly what you are looking for.
I installed SK Sync and I followed all the steps correctly (SK Sync). The problem is when I start to sync the files, nothing happens. It seems like the client on the Droid won't read or can't see the files on my server (which are mp3 files). I've tried several times switching the synchronization configuration, but nothing still happens. It doesn't seem to be a problem with my network either since I can connect to it and it doesn't give me a connection error. I just don't know why it won't detect the files.
Anyway, I did find a bluetooth synching app called Bluetooth File Transfer in the market. I installed and tested it and it works. It doesn't sync automatically though. Plus, obviously you would need a bluetooth connection from you computer.