Tip: don't ask an insurance salesman if you need insurance.

If you wish to pay anything from other accounts and I do that with a few things like utilities, insurance, etc, then I use my banks tagging feature to tag the transaction to annotate what the transaction is for.

A 50 unit building has one property tax bill and one insurance bill.

When I show my rental to potential buyers I give them 3 years of rental history with the average utility expenses and what I paid for taxes and insurance over those last three years as well. 

If the seller is out of the county you may be out of luck with them BUT...both agents should have E&O insurance.

Then your going to have closing costs, and $3500 in upfront pmi on an fha loan, and they will want to see you have 3-4000 in reserves in an account somewhere so your not maxing yourself out then most insurance companies will want the first year in advance so there's another 1000$. 

And as for the house --it's in Quincy--south of Boston --walking distance to public transportation --right in Quincy Center--there is a major development under way.Current Rents $39.3K a year (probably a bit low still)Taxes/Insurance $11K a yearWater Sewer $1200 a yearI've never had a vacancy in 10+ years but accounting for 5% vacancy this gets to NOI of $25.1K per YearAsking Price:  $630K.  

Your lender should have a few contractors they have already approved for 203k jobs, but any competent, insured gc experienced in rehab start/renovations should qualify.

Need ideas on how to proceed.

The only thing I can think of is shop around for different insurance, and make sure your property tax assessment is at or below the appraised value of your refinance.