I believe the area I'm looking at (Everett) will see an increase in property values within the next few years due to a new resort/casino "The Encore Boston Harbor" and its close proximity to Downtown Boston (2mi).There are currently 2 family (4bd/2br) homes on the market for 500-600k.

If they frequently go opposite directions, or appear completely un-correlated, then you've got a potential problem - you don't want your payment going up at the same time as rents go down!

The city checks AirBandB and similar pages frequently, fines are very high. 

@Trent Jackson - Yes, our team works with out of state investors frequently. 

(I am also required to owner-occupy as I intend to use a VA loan.)I'm frequently running into the problem of both units being occupied and a scarcity of duplexes with one side vacant.

And then there is the fact that you are looking to wholesale, which frequently means not taking title at all and simply assigning your contract, thereby needing only the funds for an earnest money deposit with the seller.  

Worth noting 4/5 of my tenants are african american and we frequently do things together.

I may as well go try my luck in the casinos, and blow it there.

I actually have some friends that live on that side of town and I pass by it frequently.

The water lines do have a problem “some times” (I was going to put frequently or often but it’s not that often.)