Stream your local music library over the internet?

So recently I was asked why I used the free internet radio service Pandora, when I had such an expansive iTunes library of music. (Literally over nine thousand songs! "What, nine thousand?!?") My answer was simple; I could not access my iTunes library, stored on my desktop, from other internet connections on my laptop. After I thought about this, I realized that it would be much nicer if I were able to access my iTunes from anywhere, so I began searching for ways to do this. I came across multiple methods, most just installing a third-party program that would stream the iTunes library over the internet, and were either not working or unfavorable. There were many more options available, but most of them involved not using iTunes, and giving up all of the functionality I need out of a media player/organizer. 

At last I had found a tutorial that seemed like it could work quite well - using a VPN (Virtual Private Network). A VPN sets up your internet connection so that you can use whatever functionality you want on the current wireless network you are connected to, but also be able to access a secondary network - the VPN - and have functionality similar to a LAN. Ideally, this gives you access to Windows filesharing services, VNC, media streaming, etc, but in a much more secure fasion than regular web connection methods.

I really liked the idea of this. I actually then had begun to make big plans for my use of it - set up a VNC server on my desktop so I didn't have to continue to mess with TeamViewer, stream my iTunes to anywhere I wanted, have access to the files on my desktop, and maybe even set up a HTTP tunnel/proxy, to get around, erm, certain proxy servers on the internet I currently use outside my home.

I immediately went to the first VPN software I knew of, as well as a candidate on LifeHacker's Hive Five top 5 VPN software list, Hamachi2. Got Hamachi set up, followed the instructions on the tutorial; it said but just enabling Home Sharing on iTunes and leaving iTunes open on the Hamachi server, the Hamachi client will be able to access the server's library from anywhere just as it would on a home network. I was quite excited to try this out. Get on the new network the next day, fire up iTunes, and am joyed to see my main library in the networked libraries list. 

Sounds like a happy ending, right? Well, no, not yet. It took at least 2-3 minutes for iTunes to even load the library list, and then whenever a song would play, it would have to rebuffer every 5 seconds, rendering it impossible to enjoy listening to a song. Yes, there's a dependence on the quality of both connection speeds, etc., blah blah blah, but I have an extremely fast, fiberoptic connection at home that has never had problems with hosting such things before, and the connection I was using outside of home was almost equally as fast, nothing that couldn't handle a simple mp3 streamed across. I also went to both computers' iTunes settings and made sure "Buffer Size" was on large, and that didn't make any difference.

So now I am stuck, a VPN sounds like the perfect, combined solution for a lot of what I want to do with my computers and remotely, etc., but I cannot find one that works, without sacrificing the functionality I really want. I was about to try OpenVPN as I saw it was LifeHacker's top pick for VPN software, but it apparently doesn't support Windows. W00t.

So. if any of my arguably existing readers have any ideas, please leave a comment below or talk directly to me, I will keep this discussion going with future posts as I develop the idea.

~BlackArrow