Without extracting equity out, these markets would have cash flow far in excess of the cheap markets that initially had better cash flow but historically have rent increases that may not even keep up with inflation.In general, when property appreciates the rents increase. 

People are far more interested in the value and extracting what they can.

Sure, you might be able to extract more value from a condo conversion, but on the flip side you are taking a significant risk, as not you have to think about and cater to the buyer, which is very different then the clients you are current catering to.Just my 2 cents.

This will enable you to increase your savings rate and allow you to focus on putting that excess in markets with both growth and cash flow where the numbers do make sense. 

This would enable you to get into the property using an FHA Loan (3.50% Down Payment) with  a total out of pocket of about 7.50% Of the Sales Price. 

But this face-to-face interaction enables me to detect if the individual is full of #$%t!.

It enables you to get last minute bookings for a couple looking to get away.

The other scenario you may want to think about is a shorter term rental strategy (Air B&B) or renting mid term to hospital workers/professionals for several months at a time - that may be more lucrative on the income side and enable cash flow, but then again you have the ebbs and flows of how often you can rent it out.

I would def say sell for another property and extract the entirety of your equity if the ROI on this property is going to drop below your target number and you can do better elsewhere. 

Figure out how to extract data from public records, if that's possible in your area.