If not, you’re probably better off with a more conventional approach.  

Explain.I really like this question for discussion Venice, but one very major factor left off is at what risk exposure. 

I have purchased an off-market property from an investor who now wants to sell the rest of his portfolio.

I personally would not invest in detroit as historically its not a appreciating market and for cash flow and I invest primarily for appreciation - I go off the location location location mantra. 

Off grid ground mount solar, battery generator, propane n septic.

It snapped off vertically down the middle when he went to the kitchen in the dark in the middle of the night and when he turned to walk back, he walked into a little cupboard door which pushed it back against an edge of the wall, which caused the wood to snap.

I held off till last April to jump into pricelabs.

Tax deductions / write-offs should be a second concern.There are some rules that you need to follow to treat a short-term rental as 'active'(non passive) income which would allow you to offset it against other forms of income such as rental income / wages.

Why pay off the mortgage early? 

I think if the house is paid off and you have a decent interest rate then you should keep it!