In places where not only won't be banned or regulated any time soon; they're actively encouraged and supported by the authorities.

The "per transaction" costs barely scale up, that needle barely moves.Ponder economy of scale for just a moment.On the loan origination side of things, my flat per loan overhead cost (compliance with gov't rules/regulations is a big part of it) is ballpark the same if it's a $100k loan or a $500k loan.

My plan is to live in one unit and do short term rentals for the other unit on Airbnb.As I was researching, I came across a short term rental regulation that owners cannot install bedroom locks in the building.

First, check into local regulations to make sure doing Airbnb in your target area is legal.

LOL  Make sure you're familiar with any local regulations that might limit STR.

The market here is crazy and the taxes and regulations make it difficult.

I unsure about Canadian Rules & Regulations, but in Texas you would have to honor the existing Lease and rules established around that lease until the lease expires.

Looking at the landlord prohibited uses list below, toward the end of the list we have 'smoking or vape store' as being prohibited so I am wondering if a cigar shop is the same as smoking shop, therefore we can't lease to a cigar shop? 

Not only do we have the federal CDC moratorium until march, 31 the state passed it's iwn set of unconstitutional rules:https://www.mass.gov/regulations/400-CMR-600-notices-to-quit-during-the-covid-19-state-of-emergencySo, now whenever you want to hive a notice to quit you have to report it to the state, give them an electronic copy and follow their procedures and firms.https://www.mass.gov/trial-court-rules/trial-court-emergency-administrative-order-20-13-trial-court-order-suspendingSuspends any eviction rules that are not consistent with court standing orders about evictionhttps://www.mass.gov/housing-court-rules/first-amended-housing-court-standing-order-6-20-temporary-modifications-toOutlines procedures for eviction cases in Housing Courthttps://www.mass.gov/districtmunicipal-court-rules/district-court-second-amended-standing-order-10-20-court-operationsOutlines procedures for eviction cases in District CourtIt seems like landlords are just becoming property managers for the state.

Job growth remains consistent, and new construction regulation is tightening and getting more expensive.