Many other investors have asked themselves (and others this question) but what I believe it ultimately comes down to is what are your goals (how much money you'd like to make), are you physically able to manage it yourself and do you have the right organization and systems in place to do it on your own. 

My current situation is that I always flip with other people’s money.

While it sounds really good they don't charge a monthly PM fee, they're making money somewhere. 

It is good, but we could be making more money if both were on Airbnb.

We were paying a bookkeeper $450/month, plus the $90 QB subscription to do our books but I felt like we were still having to tell her how to categorize everything so it just didn't feel like we were getting our money's worth.

I bought this property with a private interest free loan from a friend. the person i bought it from need cash fast so i offered them a low cash offer and they accepted.I had enough money saved up to rehab the house with my savings.

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.

You will need money to put down on the property.  

Lenders want to see two years of stable income before they loan money to you.

Living closer to work saves time and money.