@Reed Baker, congratulations on surviving Bowdoin and being thoughtful about real estate investing. I'm a real estate investor and accountant in Brunswick and think it's a good market. Here's a couple thoughts:
1) The large single family homes near the college get bought up quickly (sometimes by the college). You're right in your assessment.
2) I've been watching multifamilies in town for a couple of years and most of them seem priced pretty high. Can't even hit 1% of the purchase price on rents. For this reason, we're focused on Lisbon and Lisbon Falls, neither of which are great if you're targeting Bowdoin students. Even if you did find a good deal on a multifamily, you'd have to give up 10% of your rents to a property manager as you'll soon be living in NY.
3) Buying a quad as your first investment might be a good way to go. 30 year terms with a low down payment. You'll need to check with a loan officer, however, as to whether that can be done as a partnership. I doubt it.
4) Have you considered individually buying properties? You could each buy a 2-4 unit multi-family in NY, and rent out the other units. If you each buy and live in a quad, you would each have the other three units covering the mortgage and other expenses. You could use the cash flow towards improvements or a down payment on the next property.
Hope this helps,