The E&O carriers have suffered significate losses as a result of theses Business Email Compromise frauds (BEC) as the FBI calls them and so have changed the language of the policies to exclude the loss except for the rider. 

That is a gap of $41.67/month extra you could be getting if you went back on the market.If it were me, I would compromise and raise rent to $1,213/month or some random number under $1,300 to look like you did some mathematically formula that makes sense. 

., Everett, Revere, Chelsea, Dorchester, other B/C neighborhoods, out of state) and rent in my desired areaIf you were in my shoes, what might you do (aside from compromising on my desired location and house hacking a MF in a B/C neighborhood)?

., Everett, Revere, Chelsea, Dorchester, other B/C neighborhoods, out of state) and rent in my desired areaIf you were in my shoes, what might you do (aside from compromising on my desired location and house hacking a MF in a B/C neighborhood)?

Compromising screening standards to rent a property faster or at higher rents is a big mistake.

Income is prob ~ $150k/yr not counting any margin we'd have if our OO 3fam was fully rented.How does one navigate this sequence of purchases without compromising our ability to borrow?

It might be a good idea for you to contact property managers and owners of other STR and see if you can all agree on a compromise that would work for those wanting more regulation and STR owners.

They will clean out roots or debris, but the pipe itself can't be compromised.

Further ONLY one title company would insure us because we included rights of way in the lots 15k sq ft so the building envelopes were really about 7k sq ft ( compromise for the city). 

I"m seeking to rezone the lots as they are pre-existing, prior to the first zoning codes, which later came in and only granted duplex zoning, so these are legal, non-conforming but can't be converted to separate up/down "condo" sales as lenders won't loan if a structure can't be rebuilt after a catastrophic loss unless its zoned correctly as their collateral is compromised and that is the case in the county where these are located.