Considering long-term rental as a better option, I listed the property, but after three months on the market and only receiving low offers, I'm reevaluating.

As the city experiences heightened attention and an influx of visitors, local businesses thrive, and the economy receives a boost.

Straight cash on cash 12-15% typical, can go as high as 20%.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+, zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680, some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Is the $5k cost an actual quote you received or just an assumption?  

If we have turned the unit in the past five years, then we can typically get it done for under $1,000.

The rent is typically 1.5x that of long term rentals. 

The city estimates it will receive $320,000 in fee-related revenue over the next four years.The ordinance also limits how many “type 2” short-term rentals can exist within a certain area.

They sell these all the time.Just be aware they typically want 80% of FMV for the assets though and you still need to foreclose. 

Developers do well because they typically are not building one or two units.