Ensure the sublease is explicitly permitted in a written agreement with your friend and aligns with local STR laws.

This is why the big corp builders or regionals control so much of the larger developmentsthe deals i funded are 34 lots 160 lots and 80 lots respectively and each of them have contracts on them by Toll and Lennar and one regional but they only close when we have permits in hand. 

I was an electrician for over 20 years with my last electrical job being shop foreman for a custom electrical control panel shop and UL 508 specialist.

As an example, we decided to replace the windows in a house we were renovating and ended up costing us $50,000 extra because we got into issues with permitting and suddenly found ourselves having to hire an architect, speciality contractors, etc.  

I'm an Architect and MRED Grad and have entitled and permitted over 200 units across Bay Area and Norther California, ask me anything about SB9 or ADU design / permitting

Their customer relations person quit and you can NEVER talk to someone in person.  

Our actual carriers used to be Secura, but they seem to be getting out of a lot of insurance lines or pricing so high as to have customers drop off, and we just moved policies in Nov. to Hanover Insurance. 

That's it, but a) print out a page for each property you think is comparable, b) make the list of repairs long and inclusive of everything you've done. c) Put larger items first like kitchen remodel......and don't just say 'kitchen remodel', list things like 'custom backsplash tile/Bosch appliances/recessed can lighting/pot filler/etc. d) Cite the price/value of the work done, and don't be afraid to be generous.

It’s a good idea to speak directly with an insurance agent who understands multi-unit properties to customize coverage for your specific situation.

It is not an easy thing to run a property when your customers are horrible haha.I recommend student housing with 9 or 10 months lease and run STR during the summer for this property while students are on vacation.