I have stayed away from Everett/Chelsea/Revere for a multitude of reasons but with the massive development of large rentals/condos in Boston currently I am very cautious to look here. 

Being cautious about partnering would be a recommendation that comes immediately to mind. 

In the residential space, I'm cautiously optimistic that a "Crash" (nationwide) will be avoided. however, note that supply is even bigger here with some 900,000 single family units under construction (also concentrated in the south and west). 

Kurt is one of the principals in Sherman Bridge (correct me if I'm wrong).Kurt, as I wrote, I'm attracted to the loan, but cautious due to the information from your LO.

@Bob Roach Hi Bob, Those areas are fairly easy to rent out however you need to be cautious of condos due to the HOA fees in my opinion.

Hi Jayson -- I would be very cautious about purchasing with a 2nd home loan if your intent is to use it as a rental (whether short- or long-term). 

They are very specific about this type of thing, and the SEC is on fire right now so I would be cautious.

Could a cautious Realtor do the same before showing houses?

If I have a PM handling my property and also insuring payment, I'd be worried that the PM would be overly cautious with potential new tenants.

It is better to be cautious on your first one than getting burned by a extensive rehab.