Since this concerns your retirement, I personally would not 1031 exchange into an investment vehicle that you do not fully control yourself.

If I begin flipping, what possible issues could I be potentially exposing myself to that insurance may not protect me from and are these issues something that should concern me or are they low probability issues?

I see this as a win win, I just need to pitch it right.The main thing I'm concerned about is objections I haven't thought of yet.

Regardless of whether I'm the buyer, seller, or representing a client, what I'm most concerned about is the net cost or proceeds.    

The place is in decent shape inside and out, it's been sitting without utilities for over 100 days which is a concern to be evaluated during inspection, if I make it there.

I am just putting my immediate concerns in one email...Is there any difference between 2 story duplexes and 1 story duplexes, as in (being able to rent it, rental rates (less for one vs other), maintenance costs? 

The main part that concerned me was the fact a sign was posted but nothing was mentioned in the listing.

My biggest concern too is, what's to stop them from going around me and just purchasing it themselves without my help?

@Jonathan Gibson- that is definitely something I am concerned about here.

I would lean towards younger if you were able to tell their finances were in order.My only concern with the older tenant is that her history shows she redlines her finances, and with the average person history shows more about someone than just their willingness to change (think about how many new years resolutions go undone).