Super comprehensive coverage and easy to work with. 

You will also need Liability coverage. 

Fall back would be annual rentals.Currently (2) 2/1 and (1) 1/1 - 1,903 sqft no pool official triplex home total monthly expenses with management fee 5,710.As a STRInvestment Summary & Cash flow Payback period (years) 6.75Debt Coverage Ratio -0.51Cap Rate 9.40%Cash on Cash Return 14.82%Monthly Cash Flow $1,482 Yearly Cash Flow $17,782As Annual (self manage)Annual Gross Operating Income $57,000.00 Annual Gross Operating Expenses $5,950.00 Annual NOI $51,050.00 Annual Loan Payments $35,934.91 Monthly Cash Flow $1,259.59 Annual Cash Flow Before Tax $15,115.09 Principle Reduction In First Year $5,493.58 Appreciation in First Year $12,000.00 Cap Rate 8.51Cash On Cash Return 12.60 Returns With Principal and Appreciation Added COC Return W/Principle added 17.17%COC Return W/Appreciation added 22.60%COC Return W/Principle + Appreciation 27.17%

I even read somewhere that the additional insured is mainly used for property management companies and, understandably, have MUCH less coverage (as little as 10% of the dwelling) than the actual landlord, who should be the primary insured. 

I am interested in gaining different perspectives on how to hire an office manager and handyman so I can focus more of my time on finding properties.

STR insurance is a lot more comprehensive than a standard home owner policy.

If you have trouble finding an agent that can handle that coverage PM me and I will let you know some of the companies we use in NJ.

Some say it’s not worth it until you have a good number of properties so long as you have umbrella coverage for liabilities and such but then others say the opposite.

Same goes for any extra coverages besides STANDARD.

your lender will require "any" home/hazard insurance so perhaps ask yourself to what degree and extent you NEED coverage.