Hey, Drew -
Not sure if I can put my finger on it completely. As I mentioned, there's the vulnerability factor. Partly psychological, but also real. It's also not the most comfortable riding car, and if I'm going to an event, I'd rather drive than trailer the car. It just seemed more "fragile" than I was comfortable with.
Also, entry into the car with the top up was a pain, and I'm only 5'9", and 160#. Kinda like crawling into a pup tent!
Further, I had restored an MGB for Janet, and was looking for another project. Ever since riding in a TR8, I had been hooked on getting one. Saw one on ebay, and decided to go for it. One of the cars had to go, and since I really wanted a cruiser rather than the sidescreen, figured it was time to let it go. I enjoyed it for several years, but guess I "outgrew" it.
As I said, it's all subjective; not easy to articulate.
Got one more restoration in me, and am looking to reconnect with an Alfa Giulietta Spider. Someday...
Mickey