See if Erie Insurance services your location.

While this pertains to HUD insured and assisted multi family housing I tend to believe this to be good enough for all other property types.  

Still in the early stages of conversation but got some beginning information and wanted to see if this was worth pursing:Asking Price: $550,000 (I already assumed that was too high, trying to figure out a reasonable price to offer)Income: $4000 a month (believe there is potential for rent increase (waiting on specifics of each unit))Expenses: $900 a month (Water, Garbage, Taxes, Insurance, Maintenance, Pest, & Septic) Self- ManagedNOI: $3100 a monthCap Rate: 8.72%Stable TenantsDoesn't need major workGood Area, Decent SchoolsQuestions:1) What is a fair win-win offer?

(Plumbing, electrical, Paint and window installment)Can anyone please recommend a good reliable contractor that I can work with on this project ?

Oftentimes in Sheriff's sales the final judgement amount is published whereby you can see how much the bank is owed, including outstanding balance, interest, late fees, legal costs, corporate advances for insurance, taxes, etc. 

With long-term rentals, you are really only responsible for 4 things: Taxes, Insurance, Management, and HOA (if there is one). 

Do insurance companies make money by paying out claims?

I have enough for a down-payment or 2 for potential properties and have a partial team ready.In Connecticut before I moved to CA I was a plumber for my step-father who ran a plumbing company of his own, So I have a full team of contractors that I could use for any work my properties needed. 

My insurance agent suggested liability umbrella over my vacation rental property, "life," and my single family long term rentals with American Alternative Insurance Corporation.  

I think they work well with the insurance claim as well.