[pgsandiego]

Copied from a simular post on rennlist (the below is not my overview but is a VERY good one):

Start of quote:

1999
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Pros:
1) Significanty cheaper
2) delivers (negligibly) better performance for 2 mpg cheaper !!
3) Normal industry compliant audio system (easy to upgrade, swap out etc)

Cons:
1) out of factory warranty
2) extra miles in general due to 3 years older.
3) No glove compartment
But the side pockets and the central compartment are enough for paperwork, maps etc.
4) To a lot of people, headlights like a boxster.
Mostly to those who were bothered with this went 02+ or changed them for ~$3000 (whole job). To those who liked it or didn't matter went ahead with the 99-01.So these two groups already have their preferences setup - to there will be bias (and looks ... as they say ... are subjective!)

Personally I like that older style and passed off an opportunity last week to switch to 02+ style lights for "almost free" (due to some overlapping ~$5k work). What I totally love is the new Boxster (987) headlights ... awesome !!
5) No cup holder (!!!). Err ... yes. Not that I'm slurping sodas when driving a stick, but hey - I had to mention this !

2002+
====
Pros:
1) WARRANTY !
2) Newer car by 3 years, so chances are lower miles and lower wear 'n tear.
3) Newer headlight style (if that style tickles your fancy)
4) Glove compartment, cup holder

Cons:
1) Much more $$ than the 99's for sure
2) Slightly more gas consuption (~2 mpg) for negligibly lower performance.
3) "MOST" audio setup. MOST is an optical digital system and is a pain to deal with when upgrading since a lot of the high end (and low end) products don't work with MOST.

So the way I see it the biggest difference is in that factory warranty which you will have for a few months/years. One VERY good thing about the car industry is that you can get an 1 year older car (say 99) with 1/2 the miles for the same price or cheaper than the next years model (say 2000 or 01) with 2x the miles !!! And I believe that miles are a true indicator of a car's age and wear and tear indicator.

End of quote.