But if you have a cash buyer who is specifically looking for income property, and even more specifically a vacation rental property,  I firmly believe that there is a value add from having a working STR there.

Before you close, can the rent from your buddy and the midterm tenant cover your mortgage, taxes, insurance, plus a bit extra?

To make a new property cash flow with current prices, interest rates, taxes, and insurance, you're putting at least 40-50% down.

Taxes have to be paid, so does insurance, what about maintenance? 

Here are a few things that I like about the neighborhoods in Indy compared to other states: high rent-to-home-value ratio, consistent and gradual city development, relatively low property tax and insurance cost, affordable renovation service cost.

You can try and fight it but does not mean you will be successfulI would also be curious to see what your property insurance looks likeFor me this is just another example that home prices are gonna eventually have to soften as between taxes, insurance and Interest rates home affordability is very challenging

Be firm and follow the law, don't let her fall further behind. 

How bad is the insurance, how high are the property taxes, is there an Hoa, etc etc. 

Factor in carrying costs (utilities, taxes, insurance).2.

Insurance and LiabilityWhat type of insurance is required for a renovation project in Chicago?