I think I can broaden my search a little if I can figure out which items to focus less on. 

I would consider having an initial conversation with PMs in the area as a potential client of theirs and to "pick their brains". 

Typically a subcontractor will spell out excluded items on his proposal that he is expecting you to get.  

Most tenants respond favorably to this and we are able to resolve the matter amicably and quickly.For serious matters, when we mail by USPS First Class Mail, we pay extra to get a "Certificate of Mailing" ($1.45 by 2019 prices) to have proof we mailed the item (letter or legal notice) when we said we did.

Whenever you start conversation with your lender explain your goals and let them work on it so you have right advise from your lender.  

Some of their other big items are Condo Fee/Amenity fee, which is basically $1500/mo. 

But based on my initial conversation with him and the written quote he sent me, the landlord policy he quoted covered any loss up to the insured amount. 

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3) ok I’d either make my property manager be there for the maintenance items, or if you are self managing then you make the appointment and go there.  

Appraisers don't generally care about cosmetic items, it could have the ugliest cabinets, counters, tiles etc as long as they function.