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.  

It's a follow the leader approach.

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.

I like @Ryan Ingram approach to the early termination clause or lack thereof. 

ARV $58-$62kI've never approached a seller to make a package deal and would be interested in hearing from those that have done this.

I'm not quitting my day job (the earliest would be 8.5 years from now to claim my pension and retirement benefits) but we will look for our 3rd source of income and take the long approach to transitioning out of corporate world.Too me, this is a Marathon, not a SprintGood Luck!