Hey Evan!

The only piece I can add any value to is the pcAnwhere. I use it all the time and love it. In fact, I have clients who give me both VPN and pcAnywhere access, and I always go with the pcAnywhere. Despite conventional wisdom, I see minimal performance loss, and you have the HUGE advantage of being able to perform file transfer, which you can't generally due with pure VPN. If you have a fast network, you won't notice any performance loss.

If security is your concern, you can actually run pcAnywhere through VPN with no additional configuration (just enter the local IP). Also, if you are on a local network, which it sounds like you are, then I think (though I'm not sure) the security risks with pcAnywhere are mitigated (I'm actually not aware of any pcAnywhere security risks if you set everything up properly).

The file transfer is huge. I often hear people get around it with FTP, but when you're stressing to get a fix in, it's just one more thing to stress over (as in, oh crap - what is my FTP password again?). My recommendation would be to go with either pure pcAnywhere, or pcAnywhere over VPN.