I paid $3000 for my 05 with 30k kms, this was in the fall of 2015. It was fairly clean but I had to put about $1000 into it to get it to where I wanted it to be. Most of that was new tires.
The first owner took good care of the bike but the second, who owned it for 2 years, didnt ride much and didnt really put any work into the bike, so the rest was new cables as the originals had dried out, chain, sprockets, and fluid changes all around. If I were to do it again I'd get an 07 or newer in better condition and pay the 4 grand most people are asking for them.
Although, truth be told, if I really could do it over again I'd probably go with a Suzuki sv650.
Edit: As for the safety, i bought my bike in the late fall, registered it right away and didn't get it safetied or insured until the spring. I dont see anything wrong with that. I'm not going to put insurance on over the winter if i dont have to.