I believe my price is fair with the comps in the area.

the market is unforgiving right now, and if you buy a random property by looking on Zillow and turn it over to people you don't know to manage, you'll lose money.with respect to your specific question, if the property is safe, clean, and priced correctly, it will rent. but that doesn't mean you'll make money on it. 

That is a failure on the owner's part, for sure.  

Out of the 20 letters I've sent, I've had 1 guy get back to me and we were in discussions but weren't able to find a price that worked for the both of us.The issue is that I only have a few houses on my mailing list so far (just places I've walked or driven by that caught my attention), and blindly searching every street and address # to see which houses are actually legal multifamily will take forever and doesn't seem efficient.I know the data is publicly available, I just don't know how to aggregate it in a way that would be efficient and useful for blasting out marketing mailers.Are there any websites that can pull massive lists of all multifamily houses in my area?

Instead, there is an option period, with a (mostly) small option fee whereby the buyer can cancel the contract for ANY reason within the option period.  

Until then, it seems current tenant is on the hook and my income stream is protected by law.

Hi Conner, this is very common with MTRs.

I'd love if the property would cash-flow after we move out, but the neighborhood and appreciation potential is the biggest concern for me.

welcome @Cam Caraher and congrats on joining BP, this place is the start for many, sure was for me longer ago than I care to admit.I'm not personally in your market, although was born in dorchester and grew up in NH, but this is a great place to meet locals.If you have not already a great starting point is the Meetups posted here, just search for your area and see if any meetups are happening. 

So, the short answer is yes, but here is more:1.