(Property Meld for one)--- Owners often think a PMC can just enter a tenant's home to make repairs, but don't really understand the potential legal issues of entering when a tenant is not home.--- Owners don't understand the percentage of maintenance appointments tenants miss!

I had the opportunity to talk with the owner and he's a great guy, he did his best to make sure I was well taken care of. 

Even still, it could be said that I've still lost money due to my time on the tools instead of prospecting as a real estate agent (the cost of lost opportunity).If you can truly do 80%-90% of the work yourself (at acceptable quality levels) and you aren't sacrificing your time where you can get better returns for your efforts, then yes, it can work even up here in Canada.

I'm not sure if that would bring in enough money but it would certainly make things easier financially speaking while you built up your real estate portfolio. 

Nate I would use a low money down owner occ 2-4 unit loan which allows the highest DTI possible.

Also, don’t stress about making your first deal perfect.

That makes a big difference in the answer to what Charles eloquently referenced regarding confidence in your ability to close. 

The biggest question you need to ask yourself is if you are doing this to afford a property you otherwise couldn’t afford or to save money period, that will lead to very different conclusions about where/if to buy. 

Just make sure you set up a LLC to rack up the required experience.

Take a bit of that money and invest in learning - go to meetups and the many events that take place related to investing in the city - some for free and some paid.