A 360 is a good car to start your FLife and is driveable every day. Go for it!
I had a friend who drove his 328 daily (may be less expensive than a 360, but only marginally I suspect).
I own a TR as well and would never consider using it as a DD.
Good group of people here on FLife should make you feel very welcomed.
I was looking at a 328, but my dad refuses to let me buy one since he's the one dishing out the cash (he thinks it will break down a lot more than a 360/maintenance and servicing will be more expensive). And nice talking to you! Just from the start, the people here seem nicer than at the other forum (you can probably guess what it is but I don't think I'm allowed to say it).
5k a year is not that much, so thats not the problem... But i dont know about the weather in the area you live... In snow i wouldnt drive it...
And the maintanance costs will be a lot higher then your current car..
But for sure its freakin awesome to have your own Ferrari at 17yrs old!!
Good luck with your choice!
I live in NC, and it rarely snows. When it does, it's hardly more than an inch, and it doesn't stick (melts away in minutes). Since I will live on campus, I won't have to worry about snow-driving unless there is something I absolutely need. Also, I will probably buy a nice cover for it! And this will be a first for my family and I. My dad had a Murcielago Spider, and sold it last month, in order to pay for my 60k/year college tuition. I ended up getting a scholarship, so he figured that it would be "fair" if I got some of the money that he would be saving. He has never had a Ferrari, only Lambos and Mercs, so he probably wants it just as much as me. But since it will be primarily mine, I want to make sure I can drive it regularly, and safely put on 40k miles by 2020.
Also about maintenance: I currently have a 2010 C63 AMG, and the maintenance is already pretty bad, maybe $1-2k annually, plus other goodies that I need such as tires etc, so how much higher will the 360 be?
Insurance: Since it's on my dad's insurance and he has it listed that I drive his cars, it will only be going up like $40, since my dad and I have been safe drivers (I haven't been in a wreck, he hasn't been in one for 8 years).