2000S or a 2010 Base - Need Advice

[garv214]

I am contemplating my first Boxster purchase. I have driven over a half dozen cars now and have 2 cars in mind right now. I don't have a ton of Boxster knowledge, but I have been reading the forums and doing my research over the past month or so, but I want you folks to share your thoughts on this to help me get my mind around a purchase decision.

Car #1: 2000 Boxster S
This car is being sold by the son of the 2nd owner (his dad has been diagnosed with dementia). I love the dark blue color (my boss had one back in 1998 and I have a soft spot for that color...), the paint and top are in good shape. The car has 37K original miles and a Tiptronic transmission. However... there are no maintenance records available on the car at this time (they may exist, but at the dad's house), and I can see the following work is needed (with an estimated cost to address):
Front Windshield (12" crack): $750
Rear Plastic window (crazed/cracked): $750
Tires/Alignment (tires are old/hard: $1,000
Major Service (car is likely due): $1,000
Only 1 key, "Frunk" struts need replacing: $500 for both
IMS/RMS/AOS (no idea if done, assume needs to be done): $4,000
Brakes (unknown, assume all new pads/rotors needed): $2,000

The guy was given a verbal estimate by CarMax for $10K, but given the cars needs, I cannot see them offering him more than $7K as it sits.

So, assuming a $7-8K purchase price and no surprises turning up in a PPI (yet to be performed), I figure I will be into this car for about $18K.

Car #2 2010 Boxster Base

This car is a certified car at a local dealership (in SF Bay Area). It has 47K miles and the dealer is asking $27.9K. The car has been sitting for 9 months (according to CarGurus). The car drives wonderfully, and I reviewed the CPO paperwork (tires at 8/32" brakes = 100% pad life remaining). I would figure that I can get it around $23-24K ($5-6K premium over the 2000 Boxster S)

Boxster S Advantages:
Cheaper buy-in
Less expensive to get "up to snuff"
Car has more/less fully depreciated
Broader market interest in the 986 S cars (although maybe not as much in a tiptronic car)
Low Mileage

Boxster S Disadvantages:
10 years older
More potential stuff to wear out/fail simply due to age
Plastic rear window
IMS (unless I spring for "the solution")
No CPO warranty (2 years unlimited mileage for the 2010)
Doesn't have the benefit of the redesign/improvements in the 987's

The car would be used primarily as a weekend car (I walk to work...) and "fun" excursion car... I am a checkbook mechanic, so I am on the hook for any repairs that come up (the CPO delays that for 2 years at least...).

What are your thoughts? 986 or 987 and why?

Thanks

Gary B