Thanks for all your input guys! It's nice to hear the names of familiar places and listen to what other people in this strange place are thinking and doing.
@Angel Rosado I did go to a meet up in the city, which was amazing! @Brandon Turner spoke! Keep up the hard work, and we'll get there!
@Justin Wright I love Ossining. I think it's a wonderful hidden gem. I have found that many of the readily available properties are two-unit homes, when I'm looking to start off with a 3-unit. I wouldn't mind moving there someday though :)
@John Merryman it's hard to know how much a prison will (or will not) affect home values. I grew up in Connecticut with a prison in town, but home values (and taxes) stayed strong because the school system was so good. Ossining is not a shining star when it comes to schools, but you never know what may happen as things develop.
I also like Peekskill and would totally be willing to move there myself one day. I would look to invest there now if it were just a litttttle farther south. Since I will be living in my investment and have a job in the city, I think the commute would push me to the breaking point. The prices are very appealing though, and I would look into it more if I were you.