If your property is ready to rent I would list on both simultaneously. 

I would just go on VRBO (or similar) and look how people design their properties where it really matters (they are trying to rent to daily guests and design/amenities are super important.

Because here, the proposal would increase property taxes about 5x.  

We never collected any money for rent from anyone. 

Many months of costly vacancy, local market rent & resale deteriation, special assessments, property taxes and maintanance fees suggest a quick sale would have been the wise thing to do 2 years ago.

The fact you brought this up on this board with this situation tells me that you are fairly new to renting by the room.  

Louis, Missouri-based property manager seeking investors and opportunities to property Tenant screening, lease negotiation, property maintenance, rent collection. 

Once you complete and rent/stabilize, you should easily be able to get into a DSCR loan.

You should reach out to @Melissa Haworth she can get the actual numbers/rents on STRs in the area to help run your comps.Each building is different, each area is different, it is important to find accurate data to make good decisions.

This goes the same for calculating rents in the area, I what to know the real data.. i.e. from the MLS, or insurance from the broker/insurance agent to make the right decision.