Investing in building knowledge, your health, and your dreams will be the root of all your other accomplishments. 

What about family, sure makes visits less often and coming back for a week or two can blow the savings difference, consider health issues out of country and where are you going to end up, shipping the casket sure increases final expenses.The question isn't really can you retire, yes you can retire, the question is more to the quality of life to expect. :)       

I think narrowing down the specific market will help immensely with the next steps moving forward.

This exclusion can be used once every two years.Partial Exclusion for Reduced Use: If your dad is selling his home due to a change in health, employment, or unforeseen circumstances before meeting the two-year ownership and residence requirement, he may be eligible for a reduced exclusion based on the time he lived in the home.Purchase of a Smaller Home: While your dad intends to purchase a new home worth less than his current one, this won't qualify as a 1031 Exchange (like-kind exchange) since personal residences don't qualify for this type of exchange.

This gives me a ton of confidence in our market health. 

Health Insurance companies on the other hand have a different reputation.  

Have a good history of doing flips but had some serious health issues which caused me to be out of the game for a few years.

Have you considered eXp Realty that also offers stock, health care and alternative revenue streams? 

You have seen a lot of companies such as Amazon, Lockheed Martin, dollar general and Orlando health expand major operations out here.

Most the cases that I hear about are where there are clear violations in health standards and eviction disputes are pretty straightforward that you should be able to go to small claims and discuss w/o a lawyerHiring a PM company though will protect you if you're concerned