They don't sell the new one here. I have an 06 I bought used. I think the only other year you can get in the US is an 04. It's a pretty powerful bike. I would probably recommend the Suzuki SV650 because they are cheaper, more parts are available, and the V-Twin engine is more forgiving. I found the in-line 4 throttle response a little abrupt.
It was my first street bike, but I had off-road riding experience. I love the bike though - I get compliments on it all the time. It's just a great performing, reliable, all around solid Honda product. Check out the Bay Area Riders Forum and there are also websites dedicated specifically to the 599 - also called the Hornet. There is also the 919 but with your experience level you should stay away from that for sure.
Insurance is far cheaper than a faired sport bike too. Make sure you take the MSF class like you said you planned too, and know ahead of time that you need to set aside at least another grand or more for good gear. It is your life and your face so don't cheap out.
