It's kind of disconcerting when I can only raise rents by 5% but insurance is increasing by 10% to 15% per year. 

This decision increased our budget from $15K to $45K, but it turned out to be a wise investment.The increased budget allowed us to enhance the property's overall value significantly, and we were able to sell it for a much higher price than initially anticipated.

This decision increased our budget from $15K to $45K, but it turned out to be a wise investment.The increased budget allowed us to enhance the property's overall value significantly, and we were able to sell it for a much higher price than initially anticipated.

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.