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Sounds like you have done a lot of maintenance and any replacement car might need some of the things you cited too at the same mileage or age.
There is absolutely no way of predicting the future of your car even if we had a history to include maintenance and prior driver's habits, there are just too many variables.
And my experience might be one end of the bell curve of probability and you may land on the other end.
I owned 2 986s, taken in total they were, over a period of 6+ years, the most reliable and cheap to maintain cars I owned during the same period (and the others were renowned for their reliability). Never left me stranded. I even include in their costs the maintenance I overdid and overpaid for (best tires, not cheapest. more frequent oil changes. etc) things I didn't do for the other cars. Yes as cars age, things age too especially plastic parts. So I see an AOS in your future and maybe rear axle rubber boots. But you bought a $55k car for $13k and sure it will take some money to maintain it but you have already done some big things.
I divided maintenance into three groups: things I could do, things that didn't need a Porsche specialist but which needed a lift or tool I didn't have and the rare problem that needed a Porsche specialist (there was only one of those once I got the cars into shape).
Will an S2000 give you the same pleasure? Drive one for a while, I did and it wasn't for me.
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