You want to find a strategy that not only accommodates your current holdings, but your future goals as well. 

My realtor mentioned the later that works with the local title insurance, but when the realtor spoke to her about my situation she said I needed to check with a CPA to see if my sale would qualify as a 1031 and that she is just the "accommodator" of the money as it exchanges hands.

I know Proper is specifically cited for its comprehensive coverage, which is detailed very well on their quote -- everything from liquor liability to assault to sinkholes... 

Gatlinburg is on fire because the properties can accommodate nearly any budget and it’s a great place to visit due to many reasons like the rural aspect.

Detailed Inspection Report: Ensure you get a comprehensive report that outlines what needs to be fixed, if anything.Gathering More Information:- Talk to the Seller: Understanding the history of the repairs and any challenges they faced can provide valuable context.- Review Historical Permits: Check with local building authorities to see if the previous owner obtained the necessary permits for the repairs.

As vacation rental operators in this market, we aren't just renting sleeping accommodations.

There is no garage currently at our primary so we need to build one anyways to accommodate my tools and our cars.

Instead look at the total return and rank them that way for a more comprehensive list of your properties. 

For older demographics, consider the availability of medical centers, entertainment, and restaurants.Buildings/Permits: Assess the city's growth compared to previous years.Determine if the city can accommodate future supply.Government Regulations: Examine the city's efforts and the type of businesses they are targeting.

The CPA's above seem to have answered your question comprehensively, and just to summarize, you don't necessarily have you wait 5 full years, just fulfill 2 years of primary occupancy *within* the last 5 years.