He "doesn't want to scare off his tenants if the deal falls through." 

PLEASE NOTE: I want to sell by mid-October and with current market volatility, considering renting for a year if necessary and listening as Rent/Sell.Upsides to RentingLuxury condo that presents well, in a growing neighborhood that should appreciate well.3.375% 30 year fixedWilling to hold long termDownsides to RentingNon homestead taxes will be 14K Annually!

Sometimes they're suspended for not paying taxes or other reasons.  

Worse case they pay taxes on the money they get to keep.  

PLEASE NOTE: I want to sell by mid-October and with current market volatility, considering renting for a year if necessary and listening as Rent/Sell.Upsides to RentingLuxury condo that presents well, in a growing neighborhood that should appreciate well.3.375% 30 year fixedWilling to hold long termDownsides to RentingNon homestead taxes will be 14K Annually!

Off market preferably 

But when I have an appraiser come back with comps from a year ago from when I purchased the building and then they refuse to recalculate based off of recent comps, I'm not going to be interested in working with that person again.

HOA is about $400 a month and I need to cover 2 years property taxes and back HOA to keep foreclosure at bay while holding or until a sale.

The high HOA fees plus taxes plus wear and tear and the intense Airbnb competition (tons of units) in Miami make it difficult.

There are no taxes to worry about until distribution (pre-tax) and no taxes at all on the gains in the Roth.