PL is obviously a sports car enthusiast who found a 986 at his nexus of needs at a certain point in his life.
Crono sounds like a 986 enthusiast who is somewhat married to his car, for whatever reasons of emotions vs practicality.
I am with you Crono, I too drank the 986 coolaid. My funmobile budget was for about $10K more than I spent at initial purchase, which would have easily put me into a 987 or 996. But I liked my 986 better, and had a little left over to do some tweaking. The engineer in me likes the midengine. The artist and lover in me likes that sexy body and sweet color combo I got, which btw, is to my eye, muuuch nicer than the alternatives available then (981 wasn't out). The consumer in me likes getting a highly optioned mid-$70K in very good shape for less than $15K. And being able to feel the road, drop the top, carve up the road, and get some vitamin D while listening to a symphonic engine note... well I'm very pleased with my car. I didn't buy it to resell, trade-up, or cash in my insurance with a wreck. It is an indulgence for me, one of relatively few. I accept the risk of losing money. In fact, as PL pointed out, it is a virtual certainly that I will lose money just maintaining the thing. So the question becomes how to lose it in a way that brings me pleasure.
I suspect this is where Crono is at. There is a certain pleasure that also comes from seeing potential and carefully developing that potential to unlock it, especially if this adds to a unique and superior experience. And a more mature pleasure that comes from learning the nuances -both good and bad- of a car with which one has experience over time. You can't do this by changing models frequently, it is like tossing out the body of experience, muscle memory, threat awareness, etc, that has built up subconsciously with your car. Not unlike with my wife
Now back to the question: Looking at my car makes me want to drive it. I am not very anal by Porsche standards about my ride. But if the lack of show dampens your enthusiasm, then you have purchased less pleasure for your buck and may be less motivated to enjoy your car and to spend on your car in other areas. A seriously ugly car can limit how you use it. I will always want more go, but realistically, unless I decide to start racing it is not a limiting factor in my fun, b/c I just can't give this thing a proper workout on public roads without risking jail time.
So I would say 1) power to you 2) if the "show" ever keeps it parked, then address this first 3) if not, it is more practical to handle the "go" first.