Hello,  Your friend should look into foreign national mortgages. 

Thank god for the naysayers, if they were all fully on board with real estate returns would be much less.That said, the negative forces are real and best avoided in my opinion.

But I do sometimes wonder if we are going to end up with some board, appointed unilaterally by the president, who sit for 10 year terms, and answer to no one but themselves, and are the "tsars of housing" in America.

Your own work ethic will determine how long you can feasibly keep your head on straight at your current job.I can offer you small advice for when you do plan to exit (I am currently in this same situation)Make sure your wife is on board! 

If that doesn't works, I post on specific Facebook boards that are tailored to the same types of people who I rent to now (mostly Disney employees)

Secondly if the OP was illegally brokering (stealing my business as you say) then decided to get his license and continue brokering above board he'd still be taking business away from me, wouldn't he?

I started at a large national bank originating and underwriting loans for large institutional clients, $10M - $300M type deals.

HOA boards can be a fickle bunch, and unless you're running the show, you have no control over the fees they levy.On the other hand, your capex budget is already 18%, so maybe you're good there. 

First National Bank of PA is great.

I think this loan is Wisconsin specific, but might be part of a national program.