Unless the item is a total fabrication.  

So of the total interest you paid on that HELOC 62% (80k/130k) won't be deductible.

I’m no longer house hacking, and all three units are rented out, generating a total of $8,200/month in rental income.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

I don't remember exactly but it was around $10k total for labor and the 2 new boilers.

Yes, you should screen all tenants over 18 and make sure to note the total number of occupants.

The way I did it is I built up total confidence through first education and second entrepreneurship.  

Consider using an FHA loan to secure a 1–4 unit property with just 3.5% down and take advantage of tax benefits by living there for at least two years.

I stupidly allowed myself to get sucked into buying all his courses... one right after another... each time, thinking that "this next course" was going to be the one that fills in the gaps... only to experience yet another huge letdown... and feeling like a total putz (or like Charlie Brown to Joe McCall's "Lucy") for falling for his BS once again...

The area has certain advantages like shelter from regulation risk (pretty much as low as anywhere in the country if you buy in the approved STR tourist zones) and long term security (people aren't going to stop going to Orlando anytime soon).