The last two investment properties I have purchased was for cash, so I must have made the absentee high equity owner list.

Welcome, by the way~ I highly recommend the podcasts.  

I have a team of highly experienced permit expeditors who are well-versed about all the current laws regarding building permits and paperwork in Florida.

It would be $1.1m, and according to AirDNA it would run -$40k/yr as an STR, and while local rent rates are high it would still run about -$2500k/m.It is such a cool and unique property I hate to let it go and would love to find a creative use for it that could at least carry itself (approx $6k/m+).

I’d recommend steering away from condos due to high HOA fees, which can eat into returns.

I buy commercial grade bed frames, couches, etc when possible. 

I skipped the property since having good property manager is a high priority criteria when going forward with property.

Quote from @Zachary Deal: A lot of investors utilize the BRRRR strategy in those markets as there is relatively high rents compared to the value of the properties!  

Will add though, that a good PMC will immediately alert an owner about what their property really is and the expected challenges.Unfortunately, a decent portion of the time we do this, owners either don't want to believe the Evaluation Video we send them or decide to sell.

I have owned iand self managed all for 8 years.As for point 1, I agree there is a higher demand for Gatlinburg, but it isn't that high to be called ground zero.