The shorter the prepayment term has an impact on increasing the rate.4.

Quote from @Marc Shin: @Keagan Scott on any advice you have to help me increase my bookings would be appreciated! 

But once I got the bills, I increased the rent with the tenant's approval and signed an addendum to the lease stating the rent increase would be X and the owner would take over utilities.

That then registers the property at a new “base rate” and your future rent increases all be “base rate” + Inflation as guided by the town.

This would increase the benefit to where the fee would not be so outrageous that it would hinder the investment.

My recommendation would be to increase your deductible to a level just below painful, have your properties 4-point clean, consider your FICO because providers will, and shop coverage. 

If you spend time learning how to manage well, your income will increase, you'll save time, and you'll maintain your sanity with the courage to expand.

Yeap, exactly same as Zillow's Zestimate increased the price of houses.

As rental rates increase, cash flow becomes strongly positive.  

After that's under control, focus on increasing income through additional work at your current job, taking on a side hustle, or finding ways to increase income on your existing rental.At the same time, educate yourself.