As with any great endeavor, you first need a plan. I have already said that due to the length of time between my last ride and now that a safety course just made sense. At least it made sense to me many of the folks I talked to about this (including the people giving the course) found it curious that I would spend the money on the course when I already had the endorsement on my license. So the course was a must do.
What was next in my plan? Buy a small (700cc or so), light, cheap bike to practice on. I was not going to finish the course and then rush into a $20K Harley-Davidson with all the bells and whistles. What I felt I needed was something along the lines of a used Honda Shadow. The bike has a good rep for reliability and ease of handling. Two others I may look at are the Rebel and Nighthawk, also Honda's.
If this stage goes well, then I will rent a Harley-Davidson for a few days to get the feel for a larger cruising bike. Then, when the deal and money is right, I buy one.
Of course at each stage I will be evaluating how much I enjoy the experience and if it is worth what I am investing.
In my younger days I would already have the Harley sitting in the driveway and it may have already had a scratch or two on it from laying it down. With age comes a little wisdom. I think I have a good plan.