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Boomers are looking to retire in masses, so you have a huge pool of potential sellers.

Concerns: Although the cashflow is good, we weren't sure it's valuation and potential for appreciation since there is no good comp like this property in the area.

@Ben Cochran I hope you have factored STR tax savings into your cashflow and ROI as it can be significant.Leveraging equity to purchase a short-term rental (STR) in Tampa Bay can diversify your portfolio and potentially generate strong cash flow, but it also increases your financial risk.While your properties hold significant equity, adding debt from HELOCs or a DSCR loan could strain your finances if STR performance fluctuates or costs rise.

There is no shame in taking some time to hunker down and reassess everything, and potentially sell. 

Mike, My recommendation would be during due diligence for a potential purchase, ask for past 12 months of all utility bills, property taxes, and any other municipal requirements like rental permits, occupancy inspections etc. 

I would also be curious to see what the market rents in the area are to see what the potential upside is. 

Because you sign a lease with a poorly written clause, you still have to abide by it, and trying to get out of a legal lease will cost you at least your deposit...if not potentially more. 

@Tom EvansCongrats on the potential STR in AZ.As for a shared well agreement, they can be tricky (even when it does not involve STR usage).

@Brandon Ortiz: each strategy has its own risks and potential rewards.Owning rentals, you have the constant maintenance and tenant risk associated with owning property.