1)  Refinance property @ 90% ltv which leaves me with $157k (closing costs included in the new loan) but would be -$300 in cash flow in my current property.               

Short term rental manager aka co-hosting fees are usually 20-30%, mid-term 17-25%, and long term property management fees are 8-10%. 

How do you typically balance cost versus quality when outfitting a property?

Opportunities in real property investment need to be evaluated individually on their own merits.  

There are lots of experienced property owners, lenders, real estate agents, attorneys, tax experts and more here so don't be shy to ask questions and I'm sure an expert in that field will be able to help.

Investors are a little bit like white blood cells in a city - they clean up the properties nobody wants or is able to take on.

If wholesaling is legal in WI without a license why is it illegal to have a property under contract without the intention of actually buying the property yourself?

My question: In the original lease it states to make payments via check or money order to the Property management office.

The shift in rate environment could also accelerate the luxury STR market as inventory is exceedingly low and jumbo rates have fallen precipitously. 

Video tours of the properties help this.