I feel that if I did switch to another software platform like Rentastic, I would have to get a new team, or expect them to learn a new system.What's your thoughts?

Diving into STR platforms like Airbnb and VRBO are definitely on my to-do list as I start narrowing things down. 

Pick a screening platform/application that makes sense for you.As for meeting the applicants, I recommend meeting them at the property to show the place to them rather than getting coffee or food with them.

I've trained people at my jobs when I was a senior accountant to controller.I've used Yardi Enterprise (old desktop client software)Yardi Voyager 6s & 7sYardi Genesis2Reason why I say you won't be able to find a tutor is because no one is going to spend $15K a year to use as a training platform to mentor and tutor people.

Meet with financial advisers/wealth managers and see what other options other than real estate there are and how to best allocate / diversify. ie have you maxed out your TFSA?

My name is Jay I'm excited to join this platform as a new investor based in Charlotte, North Carolina.

There are other platforms you could do to boost but at least those 2. 

Around this time I discovered Bigger Pockets and a bunch of real estate platforms online.

Has anyone bought from the platform?

Also, SAAS platforms are supposed to include support and service (that's the last S), but the quality varies greatly from company to company.