One other consideration, and perhaps this is too whimsical a thought; however, I have purchased vehicles before (from friends) and promised them first refusal if I decided to sell it on again. Perhaps this is worth considering if you're worried about regretting the sale? I appreciate this works better if you sell to a friend or within the community but I'd like to believe that most people would honour that request and offer you your ex-car back should they chose to sell it in the future. Of course there is no guarantee that they'll sell it but equally there is no guarantee that you'll want it back. Just a thought.
I appreciate that this doesn't solve your conundrum but perhaps it alleviates some of the concern about making a mistake?
Morgans do fill a niche that does seem to buck the trend of the constant marketing pressure to upgrade to the latest model; although, I am not certain we won't see a move towards that with future products because of a need to manage the investment / ROI. This is something quite special and definitely a positive in my mind; therefore, it would be a shame to lose it. There is too much in-built redundancy in modern products (real or perceived) and I'm not keen on it.
Perry, you mentioned Porsche, to my mind, you can achieve some of the feel of 'no need to upgrade' and driving something a little special if you look to the 993 and older. The 993 is young enough to not suffer most of the foibles associated with a classic but old enough to feel special. To a large extent, the same can be said for the 964. 1989 and older you move into classic territory but again, if cared for, they are wonderful vehicles. Whether they would fill the place of a Morgan comes down to the individual.
What I do know is that there is no such thing as automotive nirvana. I chased it for many years and the saying 'horses for courses' comes to mind. A Defender 90 does what it was intended to do very well but driving them on-road for long journeys is tiring and the moment a fast section of twisty road unfolds in front of you, a sports car would be preferable. Sitting on a motorway, at 70mph, for hours on end can be done in a noisy low sports car but I'd rather be in an efficient, comfortable, safe vehicle with the ability to listen to music, podcasts or audio books. And on and on but you get my gist. Driving for pleasure is something you have to want to do and my sign of a good car, no matter what it is, is one that you park, walk away from and then take a glance back over your shoulder at it for another look... silly but those are the cars that I enjoy the most.
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