You’ll get a better return over the long-term by putting your money in the stock market.

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.

Would it make more sense to move the money we make from selling to a different property that could potentially increase our cash flow? 

I'm considering using hard money lenders or DSCR loans, but it seems like DSCR would be a bit complex.

It's just going to cost you quite a bit of money to have your accountant prep all of them.

You are bleeding money now, but each year it might actually get worse depending on the financials. 

Anyone can live anywhere they want if they have the money, and sometimes houses are bought and then rented out without much background checking on the people moving in.

Mistakes I see people make is they plan on living there a short time and over renovate the property where they will never get the money they put into it back. 

The expert you are looking for is called a Land Surveyor, they're going to want 5k-15k, if you want to make any money on your project you need to build a house so you also need an architect, they will want 10k-50k, if you're in a hillside zone you will also need a geologist, they're going to want 10k, you will also need a biologist, they're going to want 2k-5k.

I haven't had a full-time employment for a while but I have money saved up to buy a property or two.Is anyone here living abroad also or know anyone living abroad that is not physically buying properties in the USA but abroad?