@Brendan Yu -The last thing I would do is quit my source of income, unless you are already wealthy enough to live off part of the savings and still be able to invest in a meaningful way. Personally for me, two hours away is not a big deal. Most of the homework can be done right on the Internet. Yes, you might have to drive there few times to get sense of the area, surrounding etc. With the help of a good and trusted realtor, you can invest across the country these days. Whether to quit your job and get something close by entirely depends on lot of other variables, and its your personal decision.
I have been investing in real estate for over last five years, and still have my full time job. Actually, I am at my day job right now.. (shhh...don't tell my boss..lol..) Having a full time source of income coming in is a great blessing. I don't rely on my real estate investment income to survive at all. In fact I don't even touch my real estate investment income for anything other than expenses related to the investment itself, and making more investments, of course..
Is your mom, who is a realtor, local to Westchester area? If yes, your work is half done. Why not use her expertise to tap in the real estate market. Realtors have access to great deal of information. I am sure you will be able to negotiate a better deal with a family member and make some investments as opposed to getting a realtor from the outside.
Good luck..