Whereas I just wanted a clean financial transaction.

They are obviously financially struggling which makes them high risk.

If you utilize seller financing, you can sometimes get the seller on board because they get their sales price and you get favorable loan terms2)  They don't need the cash right now (retiree, empty nester) and are financially astute enough to see how collecting interest for 5-10 years on their note can be very profitable.Which argument works completely depends on what the seller needs.   

Never allow your personal feelings to influence business decisions.

I'm likely going to be a Trustee and I'm wondering if there is any financial advantage to my Dad creating a corporate entity and transferring the house to the company, and then the company to the Trust. 

You spend more time.Start with QuickBooks, as you will know your numbers - equity and financials.

I have known real estate is one of the most proven ways to financial freedom for many years now.

I was a little worried that if I had a HELOC for the down payment then the banks or financial institutions would look at it as a loan on top of a loan.

Determine what your emergency fund (CapX) number should be, then fully fund it before you start taking money out.I know many in this forum don't go about it this way, which I also understand as well from a purely financial side.

Below, you'll find what has helped me take steps toward my pursuit of achieving financial freedom through Real Estate Investing:PodcastsGeneral Real Estate investing (I haven't listened to them all, but these were very impactful for me).