First off I’m not a realtor not that there is anything wrong whatsoever with being a realtor.

He has been a great tenant, always pays on time and no issues from him whatsoever so I definitely want to keep him. 

If you don't have that professional full time sales or marketing experience, and you will be "cutting your teeth" with this undertaking to try to be one of that 20%, I'd suggest buying 3 or 7 books on sales or marketing, and reading them all. $200 in books to make sure you aren't wasting $5000 of direct mail marketing dollars seems like a prudent choice, and even if all of your real estate undertaking still fail, at least you will be better prepared the next time to ask for a pay raise or prepare for a job hunt.

They're not quite as rare as hen's teeth, but close.   

I close conventional loans for self-employed clients all the time with no issues whatsoever. 

As easy as this sounds, it's not simple and usually like pulling teeth.

It's like pulling teeth from a chicken!

They're always in my backpack on any visit to a tenant whatsoever as an owner/landlord/general handyman.

I cut my teeth investing in dumps in C+/B- neighborhoods, moving in, fixing up myself, renting out, and repeating ...

Also, if you do NOT report your "incentives", you can have the IRS on you, and your "manager" could very well be considered an "employee", even if he trips up the stairs and knocks out his own teeth...showing YOUR room for rent.