I know someone who did the opposite. Took training, got the endorsement and then got a motorcycle. Didn't like it(or more accurately, found it too intimidating being on two wheels) and bought a Free Wheeler.
Sold my last bagger and bought a canam Spyder in 2011.It was a 1500 mile garage queen. Got an outstanding deal on it. I just thought they were crazy cool at the time. Great bike, rode it for 4-5 years, then I was over it. Bought another bagger. Here I am 2-3 years later. I liked the Spyder, but I like my Ultra more.
They gave me one for about a week while my bike was in the shop. Man I had so much fun on that thing, it was shocking. Never in a million years, did I ever think I would've typed something like this, but I had a blast.
I believe trigeezer did this very thing recently. Hopefully he'll weigh in...
Yup! Have 35,000 miles on our '12 TriGlide. It gas been great, especially on long trips with my wife. But, I missed the excitement of leaning into turns. So, I just added a '17 Road King. I am keeping the TriGlude, for looking distance 2-up riding with my wife. I've got 1,500 miles on the Road King and love it. Still haven't gone 2-up on it...but will soon.
So, I wouldn't do it differently. Still love riding the TriGlide, especially 2-up.