An experienced property manager should also be able to help you net more money and will handle the marketing, leasing and background checks.

Based on your experience, in general, what is the rational or the steps in getting into a new market.

You should schedule a call with all 4 and learn what they specialize in, the markets and how they operate.  

What options do we have for locking in purchase of the property NOW & him avoiding the tax hit of an immediate sale before it goes back on market next year.

Lower rates, more buyers in the market, more competition.

Nashville is a hot market for Rentals currently and it seems like that won't change anytime soon, and I've noticed that people are renting in Columbia and Madison quite frequently.

I answered an initial questionnaire on the website and there’s basic documentation required but it doesn’t appear to be nearly as extensive as the requirements for my conventional loans.

Its all what the market will bear .  

The seller was a foreign landlord who was behind on a few years of taxes, and the property was in C5 condition at the time of initial appraisal.

Learn the basics of financials in RE, build a strong team on the ground, understand the ins and outs of RE and what market your in, understand how to actually flip the home and what strategy you are doing (Highly recommend the BRRR) as holding homes is where the money is made.REAL ESTATE IS NOT EASY!!!