I love my 986, and actually prefer it to the 987...if in a purely hypothetical world, if the two were same age I would always go for the 986, however they are not the same age, and with age comes some condition issues and repairs. For some background, I've owned my 986 for a decade, so it was a 7 year old car when I bought it...if it was a 17 year old car (as it is now) I think I would have been more reluctant. You mentioned you are a "checkbook mechanic" (btw, I love that term) and that they car is more or less just a fun toy....given those two points, I would think the newer option would suit you better as the 986 *might* become a hobby in its own to maintain. If your looking for a hobby (not just a toy), the I would reccomended the 986...as a car and a hobby, it's a blast, but you will have to accept some additional responsibilities and start thinking of it as a "classic car".
Each person is different and asking for advice on decisions is really just looking for a way to reinforce what you already really want to do. You know yourself better than any of us, and somewhere inside you already know what you want to do. Either way, your getting a big scoop of fun, and in the end, does it matter if it's on a cone or in a cup?
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