So my question is: if I wanted to save on the recording costs, keep the deed for my records, proactively pay taxes as they're billed (would coordinate with the company I buy the CFD from), then work with the borrower to get the deed recorded under their name once they've paid off the contract--am I putting myself at risk? 

Usually insurance companies only cover loss if the property is uninhabitable.

Note:The buyer is 94...I think we'd probably prefer they seller finance more of it to help with tax burden? 

Yup you would, It is nike.Now look at this graph.The reviews tap is in between the how it works and the our company tab.It is not the most popular tab.

Has anyone considered using a company like Curbio to flip houses?

Explain to umbrella company exactly the REAL facts.

Or any other company you can refer me to for 90 day late leads? 

I've contacted property management companies as well and have scheduled meetings with them as well.

Since my main profession is office management for a residential remodeling company, would flipping to build up more capital be a better place to start?

I’ve started with a title company today as I was inquired about the property.