I’m looking into a 6 family in NJ that is on the market for 550k...the gross annual rents are $83,400...taxes are $14,489...insurance is $2,600...utilities about $2,000...repairs and maintenance about $5,000.

Won't any Refinancing Lender ask about all debt obligations (including HML loan/s)?

Insurance covers that , but there goes 2 grand in deductibles . 

The 2017 Florida StatutesTitle VICIVIL PRACTICE AND PROCEDUREChapter 83 LANDLORD AND TENANTView Entire Chapter83.51 Landlord’s obligation to maintain premises.—(1) The landlord at all times during the tenancy shall:(a) Comply with the requirements of applicable building, housing, and health codes; or(b) Where there are no applicable building, housing, or health codes, maintain the roofs, windows, doors, floors, steps, porches, exterior walls, foundations, and all other structural components in good repair and capable of resisting normal forces and loads and the plumbing in reasonable working condition.

:I've always had a desire to own investment property, but had always assumed it would be something I could do down the road a decade or so, once the kids were grown more and I had either sold my business or expanded to the point of excess cash-flow and less daily obligations. 

have a borrower who doesn't have insurance and is way behind on payments.

We also didn't have her get rental insurance when she moved in but what difference would that make if we had her get that?

Hence, the restrictions (valid IMO) in place (always paying mortgage insurance) will not be optimal if you make an above-average salary. 

Roofing contractors I've talked to also do not like wood shake as they state that insurance companies don't like it due to the fire hazard. 

So what do you all see to be the average cost of insurance and and vacancies in the area?