This next month or so while we are in the process of closing on our primary residence, will be dedicated to learning those aspects of the market and narrowing down a neighborhood to invest.

We have an e-signature platform he could enter the contracts into once he has them, but he wants it bundled.

Take a look at Zillow (or whatever your preferred platform is) at recent solds, pending sales, and currently for sale. 

For underwriting you could hire someone from Bullpen, they're a commercial real estate freelancing platform and may have what you need.

I have tried using Cozy to screen him, but the platform cannot verify his identity due to no credit history.I also tried SmartMove and ran into the same issue. 

Congrats no your success, but even more importantly your dedication, and continued education.

A few years ago I was active on here dedicated to REI.

There is whole forum category dedicated to Canadian Real Estate.

If you are not collecting money because you use a third party platform such as Airbnb, then, in my limited understanding of the law, you do not need the license. 

Also, I am sure there are rules about it and it may be different by state but I sure want to keep any deposits in a special dedicated account just for those deposits and not mix it with the operating business account.