Do you feel that cash flow increases significantly with a trade up such as this to a much more expensive property? 

Most tax preparers include in their engagement letter that you have ultimate responsibility to what is reported on the return.

You cannot finance more than what wouldve been available in the initial purchase or use any improved value or new appraisal to increase the loan amount. 

It includes energy efficient appliances as well as a gas fireplace in the living space.The use of the accelerated depreciation strategy helps real estate investors to reduce the tax liability immediately which therefore increases their bottom line due to the offsetting of income.

I cut costs,  maximized efficiencies, raised rents accordingly (that alone will increase my cash flow this year by about $1,000 per month); and streamlined landscaping/pest control/rehab work and on. 

You should consider whether the potential property value increase or other benefits outweigh this loss. 

Not paying increasingly high rents in Orlando in 2020-2021 How did you find this deal and how did you negotiate it?

I think working with an insurance broker is a great way to go to derive the most competitive quote at no cost to you.I also think that you can increase your deductible up to say 5k as well as request your tenants carry renters insurance.

>Orange County’s rates are steady, with limited increases expected until 2025.

This can make the process less stressful for the tenant and increase the chances that they will accept the cash for keys offer.