They have good customer service, good online access, and take series LLCs.

I've considered a property management company, but the cost just doesn't seem worth it although it would be convenient.

If you're seeking a reliable income stream, you should definitely consider Cleveland.

Have you considered Arizona. 

I have heard that, historically, midwest markets generally are considered cash-flow markets, as opposed to appreciation markets.

However, you can likely sell all the properties in the required timeline to do the 1031k, although that will take some effort/cooperation between multiple buyers/brokers, considering the separate markets.  

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

Something to consider, if you haven't made a decision yet, are intangibles.

It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?

@Greg StrunakA good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.