The first two we lived in and rented bedroom to supplement the mortgage.

I would supplement @Russ Seiler's endorsement with a word of caution and a recommendation that you review any "creative tactics" gleaned with a tax accountant and/or attorney before putting them into play.There are still a number of "Rent to Own" providers in Canada who are operating in a manner that is "grey" and out of step with CRA publishings.  

@Clayton MillerTo Tim's point if you house hack a property would will start to reduce your expenses and supplement your income and that would help boost your RE career. 

We are very new to the process but wanted to get into it because having a renter would allow us to supplement some extra income and help pay toward mortgage while my wife stays home with the young ones.We have inspection today and if all goes well, we'll be signing off with mortgage broker tonight.Our broker needs insurance information, but we don't quite know the best way to insure it knowing we will in the very near future rent out the basement.  

Hi BP,I'm trying to help my parents find a income property to invest in to supplement retirement.

I am a Columbus based musician looking to supplement my inconsistent income with some cash flowing rental properties. 

If it is cash flowing negatively already, you are already supplementing it now with your regular income.

I am still active duty military and investing heavily on my time off in an attempt for my passive real estate income to supplement my military income at retirement.  

The guys who want to retire; they aren't in a hurry to sell/not desperate, but like not having to pay a Realtor, AND they are interested in seller financing to supplement their income.

Budget for all of the direct and indirect expenses.Be comfortable hiring others to supplement what you do.