I would tell you to not get hung up on the looks of the SV. As you can see by the kinds of bikes owned by those recommending it, the people around you who know bikes know its a smart bike. And looking smart is 1000 times better than looking cool. Not that you are in it simply for looks, but I think you get my meaning. (Though you were looking at a Can-a-tuna, and those are ugly as home made sin.) Anyway, The SV would be a solid mount to begin with (as has been stated ad nauseum) and cheap to maintain. As far as insurance, that's like asking what one's favorite condom is. We all hate having it around, but you need to find one that fits you best. (JRMMiii uses a diaphragm for his mangina, just so you know.) I have State Farm, and though I am twice your age, I pay ~$20 a month for full coverage, $250 deductable on my RC. State Farm classes bikes (at the moment) simply by displacement. Other companies, such as Progressive, will pigeon hole you based on the style. Not that its bad, but its the busienss. (Ask Likwid.) Regardless of who you chose to insure yourself with, go take the MSF. You will never regret doing so.