I only spoke with one person so far and they scheduled for more information gathering/ rental investment calls from them this upcoming week.

Ideally you would put only one persons name on the mortgage unless you absolutely had to have both to qualify.  

It’s usually best to open a separate business checking account so your rental income and expenses stay organized and away from personal funds.

But it sounds like you should also balance your decision on what fits you and your families preference and style since you will be using it personally. 2.

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

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

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.

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

This is dependent on your personal situation and strategy.