Their insurance has asked me to return the month's payment for the remaining days of their rental (Unfortunately, I did not have a cancellation agreement).I am unsure how to handle this situation, especially since I couldn't fill the majority of the rental dates and had to offer discounts for the days I did manage to book.

Lenders usually have 30-45 day expiration dates on approval letters.

This Section will not alter any date in this Contract, unless otherwise agreed. so you wont sue at this point you will go to mediation. 

Older homes will typically have systems that are out of date - even if only partially. 

This highlights why it is also important to manage lease-end dates. 

I do feel confident in the value he has delivered to-date and have line of sight on it creating monetary value.

The original closing date was in Oct 2022.  

EXAMPLE: you can probably send out the initial eviction notice yourself and then forward to attorney if a court date is needed.Regardless, it is our opinion a landlord should START the eviction process every month a tenant is behind, no matter their excuse.

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.

Quote from @Maya Cohen: I've been searching for up-to-date estimates of the cost per sq ft for new construction of SFH & MFH in Philadelphia in 2025.