If so and the monthly payment isn't too bad then you're still moving the needle forward if your main goal is wealth generation and not just cash flow. 

I’ve received multiple quotes from insurance companies (mainly I would obtain the quotes myself).

We also have a bank account at a smaller Chicago community bank, but there technology isn't as good to be honest.I think @Jonathan Greene's main point is don't step over dollars to pick up pennies. 

That's the reason why we sign leases in person, so we can go over the main issues in person and make sure they are understood. 

I realize this comes with the STR business but if I'm going to continue to use VRBO I need to find away to attract the "good" guests and minimize the bad ones.

The irony is that this might actually attract more unscrupulous out of state investors. 

The main challenge was that there was considerable deferred maintenance.

(They have other properties throughout the area listed as "approximate location" and not just this one, but most are listed as "location" with development name, street name or near an attraction.) 

That said, my main question is, can you recommend a good mortgage brokerage company that offers all the training points you outlined in your post?

Now, either I'm not posting in the right places of i.e Cragslist / BP etc or my ads aren't as well constructed as I think they would be to attract motivated sellers.