Speculation on what may or may not happen in the next 20 years, whether you even live that long, is a entirely different animal.Condos are generally a poor investment vehicle due to unpredictable rises in condo fees and special assessment by the HOA.

We have more aligned our targeted returns with each investments risk assessment.7.

Third, assess if real estate is really for you.

Has anyone had any success pursuing lower tax assessed values? 

Excellent post timing since TravisCAD just dropped the 2019 assessments today.

You MUST do a title search.You should read this: https://easytitlesearch.com/which-liens-survive-a-florida-foreclosure/It has great information, such as: "...judgment liens, unpaid homeowner association or condominium assessments, liens for city or county services, and even mechanic’s liens by unpaid contractors who started on their jobs prior to the mortgage lien’s recordation all could survive the foreclosure sale and become the new purchaser’s responsibility."

Once it is stabilized you an can restructure the debt.With respect to Midwest or Florida, I think it would be wise to assess the risk level of both and then adjust the rate of return based upon the risk/reward. 

@May Emery Am I correct to assume home values are based on tax assessment or local averages?

You could use the tax assessment as a rough guide.

The assessed value of the property is $130,000, although there are foundation issues with the home and I believe I could pick it up for between $80,000 to $90,000 (contingent upon foundation inspection and repair estimate, of course - a previous quote put the cost of foundation repair at $20,000).