Talk to a CPA to see how it fits your plan. 

I had been dealing with them for several months due to the development of plans for a property I own.

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

[1]    You might want to think about opening 2 FDIC insured savings accounts that have no fees.

Expect to remodel kitchen and baths and put new floors down, paint, knock down a wall to open the floor plan. 

We also just purchased a house in Oliver, WI that we plan to run as a short-term rental.

The cost associated with insurance for not having 20% is peanuts compared to what you potentially can do leveraging your down payment. 

I am seeing a different insurance issue.  

Not sure if they have upgraded to desktop appraisals but if they are still doing in person appraisals , make sure you get everything (scope of work, good faith deposit, social, LLC docs, insurance, proof of prior experience, financial statements) in ASAP.

Instead of evicting them, i was thinking is there some way that I could rent it back to him for very cheap (mainly to cover just the taxes/ insurance) ie 2k a year rather than the going rate of 2k a month for similar properties.