If pests were not the issue 3 months ago then they might have infested after your arrival.

I found myself many properties that had beautiful paper returns but would require managing destructive tenants, crime-infested areas, etc to get that return. 

(Seems as though they brought with them and infestation of German cockroaches,ugh!)

Having 16 months of assured cash flow is golden.The first concern is a rodent infestation.

It has a few nice neighborhoods, just like Lowell, but the rest is drug infested with homeless people sleeping in parks, just like Lowell. 

She’d likely have avoided bedbugs, which she recent had to pay to treat, and pay to replace all her soft goods furniture, after a neighboring apartment was infested.

If he's confident that he can spot everything there is to spot, roof and gutters,  foundation, electrical, plumbing, exterior siding, vermin infestation, interior walls and finish. and you're confident that you can trust his word for it, then do it.

I remember two fire-escape break-ins in our apartment (we lived on the 4th floor), roach and rat infestations, and lots of the general chaos that goes on between neighbors of low socioeconomic strata.

Also even on mainland MA you will struggle to find a rental for under $1500 unless you're living in a crime infested area.

....but.......without a doubt, our worst tenant ever was a military guy, we suspected he was in dog fighting, and brought roaches, and then never told us about the roaches, so when he moved out, it was a crazy roach infestation,  and then he just left all he stuff/trash outside.