She passed in early 2014 and my step dad stayed in the home and remarried within a year.

Taking this step will push you to really get going. 

@Dave Foster great way to explain a reverse 1031 - it always seems to confuse people and this is a perfect way to lay it out, I may have to steal this two-step explanation in the future ;) Thanks for always adding value, even us ol' pros keep learning from you!

That prevented me from getting a HELOC on my primary residence so I imagine it will come into play here.I'm looking for advice on next steps and timing. 

What are the steps involved?

Awareness of your mindset is the first step.

The next step is clear after they express interest in the home.  

Thanks guys, yes that what my understanding too can't get loan for flipping houses from the bank.I found some private money lenders but still kind of scary.I got to the point where I have to start and I am ready for the new challenge and the risk

Have you challenge the appriser if you or your agent has some other comps? 

A Challenge at that time of year is winter is fast approaching and filling rentals in winter is harder to do.