BUT, the market is quite small and I seem to be having issues finding Sold homes near properties I analyze.

Some things I do to avoid bad situations: screen well, only have properties in good locations where people actually want to live (I find tenants behave better when they know they have a good thing going for them and that they are easily replaceable), set proper expectations, have a rock solid lease, go over it with new tenants to make sure everything is clear and agreed upon, and enforce the lease by issuing a formal notice to pay or quit every single time rent is late by even one day (and charge the late fee), or a formal notice to cure or quit every time there is a lease violation.

Thinking about doing this for a long-term rental (LTR), my concern would be having actually 'boots on the ground' to keep an eye on the properties. 

I am walking with a home inspector today and I am going to use his list of issues to make a scope of work, then I will be having GCs walk the property and give me a bid once I make a SOW.

There is the practical side of what is my tax form, and will be have to pay my accountant more than I earned from this small investment to add in another tax document.I respect trying to learn and look into new ways of doing things.

In any case, if there hadn't been any market for these deals, we wouldn't be having this conversation for sure. 

I make myself available online - basically on demand - if someone wants the latest numbers about Milwaukee and an explanation WHY the market is behaving this way at the moment it is, there are your insights - for free, whenever you have a few minutes and nothing expected in return.

How much would the sales price and interest rate be? 

My STR market was behaving so unpredictably earlier this year that I decided to just rent our STR mid term for the calendar year.

I think people tend to behave when they know there's a deposit on the line.What you're saying is encouraging, and I hope the trade off to removing our security deposit will be more bookings.