Something you can do to start your 5 year plan would be to live in your Condo for 2 years so you can qualify for the $250k tax exemption (if single) $500k if married and then take those funds to either put a down payment on another property you could live in plus you would have some left over funds from the sale.

I wonder if tax's shot up because you lost your owner occ exemptions some state non owner occ tax's are 2X 3X higher than if you live in the property.. its one of those gothcas that happens in those states.

You can sell the coop and purchase any type of real estate you want.The rule for the primary residence exemption os that you have lived in it for 2 out of the 5 years prior to selling. 

The town treats it as a commercial lodging property so it's exempt from heavy-handed local STR restrictions.The sellers have been open for biz only part time in their retirement.  

Is there a specific town or suburb that would attract medical professional and/or professional tenants more than others?

I am in the medical field and want to dip my hands into real estate.  

I just get my lists fir free from the municipalities:- Most delinquent tax payers- Tax-exempt property owners- Tax-deeded previous owners still in the redemption period- Fire-damaged etc

SELLAt this point in time you get to exempt capital gains because it was your homestead. 

I’m sure there will be a something exempting selling properties you own.

Many wont even live till 60.People get blinded by the new shiny toy that they forget, REAL ESTATE IS THE RETIREMENT VEHICLE so why put a retirement vehicle into another retirement vehicle which you can't even enjoy until you're dead or crippled with medical issues.