To make it more complicated I have 5 different management companies.

They're essentially saying the criminal laws and judicial system are racist and unfairly target minorities, therefore Landlords shouldn't consider criminal records when determining risk of an application.Question: who instituted the laws and put these judges in place? 

There is also the privacy part, but its going to get more complicated and possibly expensive if you are just self managing.

And now that money invests in real estate notes, tax-deferred until I'm old and gray (and it is far less complicated than owning real estate directly).

Less complicated and less risky.

Definitely helpful to know it's more complicated than just "cash is king."

So is wholesaling a hard process to get into or am I just making it way more complicated thinking about it in my head ?

Regardless though, they are both obviously under HOAs which can complicate things (it has for me).

Having a partner complicates things, in my opinion.

Depending on your personal tax situation, you may be better off holding property directly in your name ... your situation is further complicated by the fact you are not residing in Canada at the moment.If you did hold properties in a corporation, the retained earnings (after the company pays its taxes) are traditionally not taxed in shareowners hands until withdrawn as dividends.