Confirm that the provider has experience with the particular investments in which you intend to invest your retirement funds as you very likely will have questions in terms of the mechanics (e.g. how do you invest in real estate, etc.).4.

If not, then I don't see anything wrong with considering removing windstorm as long as you've weighed all the options.  

Where can I get private money and someone interested in purchasing 1.5 acresto split the current 3+ acres and leave the1.5 acres with the rentals for the long term deal.

What are the interest rates and loan terms typically associated with DSCR rental loans?

I would like to re-finance into long term debt once the project is finished using a DSCR type loan.

My wife an I try to focus our long term rentals in towns within a 30 - 45 minute drive to Raleigh.

Always analyze for long term numbers but in the back of my mind I look to see if it will be a good fit for possible MTR or STR.

others are pulling from the hotel pool and renting out to longterm renters for $2,300-$2,500/month.

The property will be rented out a mix of short, mid & long term rentals. 

The one thing that may cause a problem is lenders not taking the short term rental income if it has not yet been stated on your taxes.