Many times the forms you will find on the internet are not very good and/or don't address specific local concerns and requirements.

If she is interested in disposing of the property and she accepts my offer am I still in danger of a contest?

A title company where I have never business may get worried or bring up issues which may concern your refinance lender.It is best to let sleeping dogs lie so don’t tell an unknown title company the friendly loan proceeds initially came from you.It’s none of their business your terms with your lender and how you acquired the funds.My loans from a friend are not truly free, though he would do so for free.

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

Over-extending yourself and growing too quickly can be very dangerous.

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?

Knowing what I know about the region from real estate and tech industry news, which is just enough to be dangerous, I would not take any equity out.

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.