WOW;
1st: get a manual car, tell your dad to grow a pair if in fact he is keeping you from getting one (although I think you don't want one/learn how to drive one)
2nd: roof rack really? Go to the website and plug in your car parameters and it will spit out what you need. Buy all of it and then assemble reading instructions. Yakima and thule are the best in my opinion.
3rd: If you are going to be throwing stuff in your car look to get a wagon. I know when I was in the car market there were 04-05 audi wagons for like 10k and only like 70-80k in mileage. Also wagons come with roof rails typically and therefore a roof rack is even easier to install.
4th: New jettas don't cost nearly whatever ridiculous quote you said. New jettas can be had for 16.5k...whats that? Not enough glitz and glam for you? They have a few options for under 20k.
5th: What are you thinking spending that kind of money on a used car?
6th: Dope; Dope; Dope cars can be had for under 10k. Like I mentioned 05 audi's, 05 wrx's, etc. I would seriously look into getting a legacy gt etc...heck for that price you could probably land a legacy gt spec B which would be dope.
7th: If your dad has worked on cars for years he know; don't try to come online to find out what he already knows.
8th: If your dad works on said cars look into a 88 bmw 325 ix. Those cars are crazy the only problem is finding a good one. Nothing would put a bigger smile on my face than one of those. Also your peers that you are trying to impress would at least think you had some class if you drove that; and not just spoiled. Although if you are driving a 16+k car than that is probably the norm for area so why don't you want to stick out or be different. Your dad could teach you how to do any work etc I am sure and it would be a very rewarding first car...not to mention if you fix it up nice it could be actually worth more when you sell it.
9th: To that guy who said he had a saturn... that was me until it blew up...didn't have any real problems until then 190k and well; down for the count. I got around vermont alright in that with some snows.
10th: Just for reference to what could be had for a fraction of that price: I just bough a saab 92x with 80k for $8500. If you don't know what that is look it up.
11th: Dude if your smart; seriously smart you will start investing most of that money...There will be a point in your life when you need it. It may not feel like that; because as far as I can tell you have never been told no/cut off. Trust me when that money well called your parents dries up its going to suck big time...Yea sure you will probably go to college and get an economics or business degree but its tough out there dude. I will give you some advice even though you probably are hating what I am writing and are thinking that I am full of shit but trust me: SAVE AS MUCH AS YOU CAN