Also consider all lenders will require to review your insurance when underwriting a loan and it's likely a violation of your existing loan documents to let the properties go uninsured even if they didn't require insurance escrows. 

There exists those of us that want a property in Costa Rica despite the issues we are discussing here.

I'm considering a fixer upper to retain as a rental but need guidance on how to pick reputable contractors.  

You could build one but it is better in most cases to buy one already existing.

What is the best way to best way to deal with the existing tenants? 

I do not know how they are handling new customers verse the Midland existing customers.Regarding the customer service it seems the people I dealt with are still employed and only my "personal rep" as it were, was promoted and another took her place.

We were in a financial position where we could keep our existing home, upgrade, and purchase another home.

However, the buyer's bank refused to fund the loan, stating they needed to conduct a full inspection—inside and out—to confirm the property still exists.

The house I regret most for not getting it is this one,https://www.zillow.com/homedetails/N8064-975th-St-River-Fall...I was so close to getting it, but I chickened out because I have absolutely no idea how these houses even exist.

They could work with an existing lender, do some marketing to help broker, get a cut and make FARRRR more $ with zero risk vs this EMD lending.