I know some will differ here but I will offer my personal opinion like many others have.

I am really interested in meeting any in-person groups in Boston (now-May) and Chicago (September-Onwards).

We would want to use it for personal use probably one per year. 

I let the booking expire and figured it was a troll.I then get another request from the same person about a month later for the same dates.

I am still personally buying rentals but I am not expecting much in the way of cash flow at the moment.

I'd personally sell the townhouse (doesn't sound like it cashflows or would make a good rental property) - you may have no capital gains if you have lived in it the past 2 out of 5 years - I believe the first 250k for single filers is exempt from taxes and the first 500k for married couples.

Fewer still actually show-up to deliver the value in-person. 

A contract is only as good as the person enforcing it.

This is dependent on your personal situation and strategy.

Interest rates need to drop a certain amount in order for a person to make a transaction right now.