Thanks a lot for the input guys!

I'm definitely leaning more towards the GS500F, now all I need to do is find one for less than like 2k... hahaha

I've been looking around for a while and had originally decided on a 250R to get started but having just gone out and actually sat on one, I realized it is not the bike for me. I think the 500 will be a great start with a nice balance between sporty feel and not killing myself, and after talking with some people who know a little about the insurance issue, literally they said if it has an R in the name the insurance will be higher, the fact that it has an F basically drops the insurance tremendously. So that is definitely the front runner, and hopefully after a year or so of riding that and getting used to everything I can finally get my D675.
-Shift