Which one was the easiest to work with?

As an estate and gift tax advisor in a previous life this has been on the liberal agenda for 50 years, so in that regard it's really very old news.

Traditional Buy & Hold is the easiest entry point for many investors.I normally advise new investors to take some time to learn about each strategy (3-4 days is enough to learn each strategy) after that, then decide on which is best for them based on personal goals, time and personality, and other factors best known to them.Goodluck 

@Michael FrankoRecommend you don't go the family route, even though it is the easiest up front. 

What do you believe or others have told you are talents and gifts you have?

The harder part is not the software but setting up the books appropriately (at the start) to make it easiest to use in the long-run. 

That way its easy for her to get a loan (assuming that gifting a DP is still acceptable) 

What is the easiest/cheapest/best way to accomplish this?

She did leave you a gift for getting started with your real estate portfolio.

But I have the cash to gift her for the down payment and closing cost.