I was getting ready to do this but if I can get ALL of the same features, not lose any previous data, AND get my BP Pro membership all for the $32.50 per month, I'm willing to do that.Who could I speak with to help me get the information that I need because I need to make a decision in the next two weeks before my annual payment to Stessa will be due. 

Stick to areas you know well; this familiarity can greatly reduce risk and boost your confidence when making purchasing decisions. 2.

It might be a better decision to do a 75% Cashout Refinance.

And in part, it depends on the investors and capital that you have access to (this tends to play a factor in many decisions when raising outside capital).If you do want to go the fund route, you might want to consider using Avestor. 

Thank you for the detail information this is very helpful.

No decision yet, but it's looking good for the investor, as they were able to find about 20 other houses in the area that have been operated as STRs for years with no complaints.

There i a bit of research that needs to be completed early on in order to get a good judgement on the feasibility of this; from there, the "Official" way to ensure you could pursue this would be to request a "Zoning Opinion Letter" to receive an Official decision from the Department of Zoning in order to ensure this will not cause any issues during your permit review. 

I feel like there’s a balance between being decisive and being reckless, and I’d love to hear how you guys approach this.

You will not get a large enough sample size to have reliable information.

Then feel free to make a more informed decision.