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. 

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

(This single thing cost us about $6K extra in revenue. )  ARV was $160K. 

My back-of-napkin math so far seems to suggest that going for the bigger unit won't necessarily bring in a lot of extra rent, but could add a lot of value when I sell it, so I'd be absorbing a lot of extra taxes for the time I own the property.Any thoughts or insights would be appreciated,Michael

it looks like that's exactly what I'll be doing. as long as there are no big events that happen in the next 5 years it shouldn't be a problem. however it is a bit of an extra risk and I don't love the idea.

The way I ran my numbers was to cover all my costs durIng peak months with some profit and then extra profIt durIng the off season.Few Example expenses:Cleaning- needs to get done before every new renter.

Since we launched the last year has been solid  - Since we have lived on the property it only would cost us around 50 extra a month for water and utilities from what we were already paying.