Even when talking with some real estate professionals who would seem to have an incentive to help me with renting out my property, I have been met with serious warnings (they pretty much say don't do it).

Regardless of legal nuances, I can tell you from extensive professional experience: Don will WIN an IRS audit for his Subject-to interest, as long as he can show that he made the payments.

As a newcomer to this field, I am eager to learn and grow, while also contributing value to investors and professionals.

FidelFidel,When I saw your question I got interested as most Canadian investors are rather running away (or pausing) from investing in RE in Canada.But to help in your journey, here's what I can share mostly from either my personal experience or discussion with relevant professionals. 

A phone call will answer all the questions or a quick visit is better, set an appt. 

Readers should seek professional advice.

It sounds like you’re handling things well by setting up systems early.For this tenant, a calm and professional response is best to maintain a good relationship while reinforcing your policies.

So, if you have 10 units and you are going to pay $1,500 a month and you are working on an active income job, too, this is an easy switch due to the labor mentally and physically (even if it is just phone calls) to get these rentals running as a well-oiled machine.  

Hi Lucas, welcome to BO forum- you will connect with many professionals and learn a lot here. 

Call around and talk to a few people I'm pretty sure you will find someone who will make the time for you who can tell you pretty much on the phone if you could qualify and ballpark for how much.