Now for the refi, needed to have really strong income and credit with plenty of funds in the account to show proof of funds, so after all that couldn't refinance either without bringing 40% of the property value to the table.

With a few of our STRs being glamping tents and RV sites, the cost of a policy to cover a the repair/replacement of a tent or picnic table is not worth it in my opinion.

Although not classically thought of as Midwestern have you also thought of Tennessee and North Carolina?

You are asking the classic question in the MTR space: how does one evaluate what could be a good MTR.Unfortunately, MTRs are at a point similar to where STRs where 10-12 years ago, and there really isn't a one stop shop source for great data.

My Ex and I opened a restaurant on an “estimated table turn” per night that seemed reasonable based on what we thought we could get.

Is an FHA loan on the Table, or would I have trouble qualifying?

That said, it looks like you'd have to bring a huge downpayment to the table for this deal.Why not just purchase with conventional financing?

This leaves some increase on the table, but also makes it more likely that tenants won't leave over the rent increase. 

I hope you make a few connections so you can meet across the table and get the advice you need.

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