Especially after one of these scam seminars blows through town and gets a few fools to attend.

The professional who knows who they're doing for $100/hour or Bubba down the road who does it in his spare time for $15/hour, carries no liability insurance, and will not be there to make things right when your engine blows up?

The bank isn't going to let you blow their money.

The rates and terms on conventional mortgages tend to be better which is why some BP members advocate maxing those before moving onto commericial loans. 

Its important to understand how credit and debt affect all assets, but its more important to realize the signs to be able to be ready for the storms that blow through.

The fair thing to do would be to first give him the opportunity to start paying rent and remain in place - and I will do that, as long as he meets my tenant criteria following a -$1000/mo blow to his income.

I'd also throw out that our STR's earn between 2-3 times what a long term lease would bring in; so playing devil's advocate to your original post—getting your systems in place to manage it as a STR now could actually move you closer to your goal of getting away from full-time W2 income.

Otherwise, I am a big advocate for "house hacking" as it reduces your risk as well as makes managing the property a little easier. 

Primarily the kind that involves blowing out old $150k 1000 sq ft houses and replacing them with mammoth $500k houses over double the size.

Of course when the tenants out it blows the cash flow all to heck.