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. 

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. 

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.

The hardest part is getting started.

No more long term tenants with dirty yards and houses and cars up on blocks.c) Neighbors love them (except of course for the party atmosphere which has declined rapidly as AIR and VRBO have clamped down on that crowd)d) economic impact - most cities make millions more from TOT than they would without STRs, improving the quality of life for many, particularly the lower classe) the increased tourist activity brings in big $ for local restaurants, breweries, museums and the likeWell I'll stop the rant, you can see where I stand.... :-) Best of luck in your RE career if you go that path....