I found the deal, procured the sale, represented the seller (I have my RE license as well) and have 100% brought this deal to life (aside from the fiscal purchase, obviously).3.)

I'm looking for advice on how to best approach this seller and also not make a major mistake for my family. 

My problem is that I have just been holding properties for too long, some approaching 30 years. 

Any advice on how to approach my first flip?

There are both positives and negatives to this approach for the new investor; the positive being there is no better way to learn than on the job.  

By creating a conversation, I feel that it may help me understand a more detailed approach to being creative.  

I’m finally to the point where my knowledge, and drive has brought me to become the investor.

It's a follow the leader approach.

Acquired through off-market from a realtor that I have brought value to previously.It's in a great location close to the highways but with lots of land.

As she is approaching retirement, she no longer wants to manage this rental property on her own, and we were instead thinking that she could pay off my mortgage, and then I would enter a "rent-to-own" agreement with her.