I'm in the boat you want to get on (60, kids gone, my time......).
The great divide in Boxsters is
986 (inception to 2004)
987(2005 to present)
I'm a big guy and found I fit better in the 986. YMMV.
In the 986's 2003 and 2004 had some notable improvements especially the glass rear window. So my search was for a 2003 or 2004 S version. S or non S is the other big divide, S has bigger engine, more power, bigger brakes, etc.
I ended up with a low mileage excellent condition 2003 S this spring for just north of $20k, a pretty standard price.
If I had fit in the 987, I would have been looking at newer years, but still the S for the performance.
I'm sure there are many more knowledgeable people on this forum who will add to/correct the above.
Am I glad I did it? You bet.
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