i think you can ride your board a little shorter than 160-162 depending on what board you pick. you might also wanna get a mid-wide board for your boot size. because of that i'd probably go to a store and get fitted for everything. of course, i was a high school senior once and money wasn't flowing out of my butt so i can understand you might wanna shop around online and on craigslist.
with that said, if you're going casual you should spend a little more time actually trying stuff on and buying new. a lot of shops should be starting to get their sales going. paying the extra premimum to make sure everything fits you will save you a lot of potential grief since you don't yet have the luxury of disposable income. at the very least, buy your boots in-store.
spitfire's an old board, just an FYI. though i heard it's pretty good.
where in NY are you from?