Also note that the cities of Portland and South Portland (and other surrounding towns) are taking a hard look at short term rentals, and additional fees/regulations seem likely.

Local rules & regulations.

(Some rules and regulations)-Did you know you can purchase a property with a self-directed Roth IRA?

The different cities all have different regulations on short term rentals.

However, I do not know the regulations their in Canada. 

I wanted to share this article...IR-2018-206, October 19, 2018WASHINGTON —The Treasury Department and the Internal Revenue Service today issued proposed regulations and other published guidance for the new Opportunity Zone tax incentive.Opportunity Zones, created by the 2017 Tax Cuts and Jobs Act, were designed to spur investment in distressed communities throughout the country through tax benefits.

Lease Options are great in NC and there is no need to work around those pesky regulations, better to do it correctly and comply.

I am sure it is because regulations require appraisals so we don't have another financial collapse.

Maybe you should look into buying a white elephant near you, and turning it into the lowest possible level group home or "rest home", the kind that is not regulated, where you house people who are on SSI. 

The reality is Screening these areas is an art form and most of the criteria I see people on here post just won’t work in this environment.