I had 3 different long term tenants in this unit over last 13 years, never had any issues.

The $795 is not my concern, I would be more worried about them performing.

House hacking is a term some people here use to refer to getting a roommate in your own home. 

@Belinda Fello- Usually, when you rent a property that has an HOA, you have a term in your lease that requires the tenant to comply with any rules or regulations of the HOA. 

When starting, I say "borrow as much as you can for as long as you can."

The author shares a wild story about discovering his long-term tenant was secretly running an Airbnb out of his apartment.

I also converted the other side of the property (it's a functioning duplex) into an Airbnb / Short Term Rental.

I have a gutted carriage house on the back of my property, so my thought is to get my feet wet with house hacking by creating space for a longterm tenant. 

Your 20s are for taking career risks, delaying gratification, and thinking long term.

Hello - I own a duplex in Bracebridge, Ontario, Canada - the largest issue I have has been property management - I live in BC, and there are not many property management companies in Muskoka that handle long term rentals - many do air bnb properties, but most property owners who rent long term do the management on their own.