Thank you everyone for your responses!
@Shmuel Waldman, I appreciate the advice on networking. We have been doing a fair amount of networking, including building relationships with RE agents, other investors, and lenders.
@Adam Sankowski, greatly appreciate the detailed response. Congrats on the beauty of an investment in Union Square. One of my favorite local bars is actually over in that area, Brass Union. I like your analysis around the 1% test in this area and possibly opening ourselves up to additional income through AirBnb. Fyi, I do not specialize in Real Estate (yet anyways). If I come across anyone I will forward the information along to you!
@Charlie MacPherson and @Lien Vuong, after looking this weekend I can confirm what you are saying. We are finding areas along the commuter rail going north and south seem to have better cash flow opportunities and aren’t appreciating as quickly as the more immediate areas surrounding Boston. The multi-families along these commuter rail stops have been the most promising to this point in our research.
@Dick Stevens, I did not mention it in my original post, we intend to use the FHA "house hacking" approach for our first property. Otherwise we would need 20-30% down to obtain a bank loan with the sole intention of using it for an investment property, as you mentioned.
@Adam Sankowski