I see that you required contractor to have General Liability and workers comp insurance.

For the DSCR, some lenders require a period of prior investing in order to qualify for that loan, for example one prior year of investing.

As long as you meet the requirements for both statutes you can take both.

What does your lease state about landscaping and yard upkeep requirements. 

There are tons of benefits to house hacking, reduced cost of living, property management experience, lower down payment requirements etc. 

I guess you could keep refiling the deed to show change in fractional ownership...Obviously, this requires some serious looking over and structuring from a qualified professional or two, doubly so since it coming out of probate. 

You will have to become active and join a firm (affiliate) where you'll have oversight, and if you want keys to the kingdom so to speak, you'll have to subscribe to your NAR MLS, perhaps your commercial board, and all the memberships your firm requires. 

Question regarding the IRS requirements for hired contractors.

I have seen it happen a number of times.But yes it does require work and it is a slow game not a fast one.  

Most heating climate states have minimum temperature requirements you need to meet.