Depends. 

My view it’s that it’s always better building a brand rather then focussing purely on the aggregators (whether Airbnb or otherwise) but it would depend on your objectives as an investor/operator of your own spaces. 

Hi Paul, it all depends on your comfort level. 

Keep in mind the more you write off the less money you will show as you net.If you have (2) full years and depending on how the accountant files your taxes you will have a schedule C more than likely or another schedule that shows profit and loss.

It really depends on what you are looking and I think your thought process is correct.

It looks like a great idea on the surface but the numbers don't stack up from a risk/return point of view as far as I'm concerned (it could be different for you depending on your return expectations).

Yes, you'd be doing either delayed financing or a cash out refinance depending on the timing.

Depends on the actual location in Southern Illinois.

Or free up more of your time depending on your goals?

It could vary of course depending on the defenses of the tenant and if the court is presently backlogged.