You could look into buying a GD (first gen Fit 2007-2008). As wanderer said, you'll get plenty of scratches and scrapes so you might as well get some practice with touch up paint and trying to buff minor scrapes on an older car. Also, a brand spanking new 2014 Honda Fit is for sure going to stand out and be more attractive to thieves compared to a 2008.

Insurance is what it is and since you are a new driver and a male your gonna have to pay the price for the first few years.

I'd get the sport if that's what you like. There's not that much price difference and you'll for sure spend at least that much trying to soup up your fit with a body kit and aftermarket wheels. Plus the stock kit looks pretty cool. That's the great thing about the Fit, it really doesn't need that many modifications and is pretty awesome from the get go. I'd hold out on thinking about mods until you get the car; as you own it and drive it, you'll figure what you like and what you don't and want to change.

One means of deterring thieves might be to remove the Honda alloy wheels and replace them with steelies. Just kidding! Seriously, I believe it is the valuable OEM Fit sport wheels that are so attractive for thieves. If you remove them and get some aftermarket wheels, there's a lot of nice models to chose from and I don't think they are as attractive to thieves. I'd look into getting some rear tint for the windows and I NEVER leave any bag in my Fit (for fear of getting my windows smashed). I street park my Fit and sometimes I take a glance out my window if I hear noises to check on her