It is not unusual for a Property Management company to request to be put on the insurance as an Additional Interest or an Interested Party. 

I need someone that isn't too conservative.

Since they all follow the same guidelines, and it was an unbiased 3rd party, there is significantly higher chance your refi numbers will come out closer to what was expected than just trusting Realtor opinions (after all - banks don't hire them for an unbiased evaluation of homes prior to lending). 

the difficult part is not selling your old property. 

You can have a conservator, but that didn't go well for Brittany Spears. 

Can anyone speak from experience or expertise about what issues I might have by leasing the property to three parties, given I respect the occupancy limit?

As for a project update; the 4th bedroom has been added and is already leased by multiple parties until summer 2023.

I know the process is different than 3rd party management, as all will be onsite.

Collecting rent from someone oftentimes shows courts that both parties viewed this as a landlord/tenant relationship VS a squatter. 

Second part: I am an experienced contractor.