With a 3-5% down FHA loan, I snagged a cozy home in a hot spot, worked from home to play handyman, and created a hedge against the "what-ifs" of life.

@Anthony Sigala that "Rule" was created for mostly Class B properties BEFORE the Great RE Crash of 2008-2010.Values after the Crash dropped so much, that it could also be used for Class A rentals.Values are now more than their pre-crash highs, so the rule now only applies to Class B & C rentals.How are you identifying Class B & C submarkets in your area, so you can properly apply the rule to the right rentals?

I do outsource my Taxes, but I meant having a Real Estate Tax Accountant or a CPA who I chat with to help create me a long term strategy.

That said, we have traveled a lot and stayed in wonderful Airbnbs over the years and have always dreamed of creating an incredible experience for someone visiting Minnesota with a short-term rental as well, so we are definitely open to that idea and have some great experience as to what we know would provide an exceptional short-term rental experience. 

Once you're ready, create a goal (e.g., "I will buy at least one single-family home, duplex, triplex, or fourplex before the end of 2019") and then do it.

By insurability I'm referring to the problem created for title insurers evaluating what has transpired and whether they will issue a policy on the next transaction.

The fact that you can could create that desire to move.  

I hope you are working with an excellent agent or broker, they can create leverage and opportunity for you while protecting your interest. 

I know you code C++ well enough to create bitcoin. 

.-- There will be some new category of property created between residential and commercial, as @Robin Searle noted.