I spoke with the bank about given us an extra month or two before starting to pay the mortgage cos I can not afford to pay two mortgages at the same time.

What's your return on investment for the extra money needed to do the repairs and bring the property up to date? 

If someone wants to bring in a dog I would charge 100 dollars a month extra.

We are seeing a little extra inventory on the south shore, but mutli's are still in demand.

I take an honest look at what the building can support, give an extra margin of safety, and take out about that much. 

I would update your lease to include fines after an initial warning about leaving trash or personal items in the common space.I wouldn't allow tenants to mail in the rent.I allow them to deposit directly into my account, ACH or Zelle.Maybe get extra trash cans so that they don't have to leave their bagged trash by a full can.

@Ryan McGrath I think your first concern is to make sure it's a legal rooming house or to understand the steps that it will take to make it one - which I'll bet would include things like extra egresses and a sprinkler system.One incident / phone call / police visit where word gets back to the building inspector and you might find a big red "VIOLATION" sticker on your front door.Next, I'd want to do some forensic accounting. 

So I find myself in a situation where- as I learn more about BRRRR, am having difficulty in choosing what the best option is moving forward. 

Well I put in an offer and but he is having difficulty putting in the specifications that I want. 

It took 1 year to get all of the offices and the 7 extra parking spaces leased out, but now it cash flows beautifully.