I've battled with this decision as I do think the Cayman looks better than the Boxster. they are also extremely affordable now with some falling below $20k. I think it really boils down to one major advantage the 986 has: it is MUCH easier to work on than later Porsche's. If you DIY and work on your own car then "upgrading" will possibly be a regret. The 986 is very easy to work on (compared to newer Porsches) and that's something I don't want to give up.
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DD summer/winter: 2000 Boxster S
DD spring/fall: 914-6 w/ 3.0L SC Dual Webers
http://imgur.com/a/k0Wtl - My 914-6 Build/Project Story
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