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I’m planning to buy a used Boxster to base in Florida and use when I’m down for the winter season. What years, if any, should I avoid, and is there a year where reliability trended up?
My general view is buy the newest vehicle you can comfortably afford.

There are pros and cons of every version of the car and no magic bullets. If I were in the market, I would be looking for an '03-'04 model year "S" model. I would plan an early clutch and IMS job and then enjoy the car. That view incorporates a bunch of personal preferences - in particular the view that 986 models are the best to maintain, and most analog of the model history. Those are the last of the 986 breed. They do have the single row IMS - hence the early replacement. (The switch happened in the middle of the '00 MY.) In 2005, the IMS became non-serviceable. So either do a pre-2005 or post-2009 direct injection. In my view the evolutionary changes in 2003 - glass window, steering wheel, inner liner, make the '03-04 cars as good as any of the later ones. I expect the cost differential to be huge between a 2004 and a 2009+ car. Hence my thoughts. YMMV.

Very early models experienced cylinder wall problems - but that should have long resolved on any street car. The IMS bearing issue plagued all of the cars before direct injection to varying degrees. (one could write a book on that.)

the direct injection cars are generally seen as good, but the technology has its own issues with carbon buildup etc.
+1 What he said. The newer cars are not as easy to work on and the older ones are getting real long in the tooth, 03-04, which are near identical, still allow a lot of DIY but are modern enough. I am biased since I own an 03 S so take that for what it is.



Edited 1 time(s). Last edit at 03/10/2020 12:03PM by paulofto. (view changes)
Too Late.. let the biases fly.

I have an 2006 Boxster S with 63K that I have owned for 10+ years.

Pros:

2nd Year of the 987
trusty 3.2 LTR flat six,
low maintenance except for oil changes, spark plug and of course rear tires.
Low purchase price compares to a 2008 as you shouldn't buy the 1st year of the a new model or engine change
2006 was noted as the least problematic Boxster

Cons:

2006 was a bad year for the water pump -Replaced @ 43K
If you need to replace your IMS, the engine will need to be lifted out and crack open the case. No issues as of this report
No Porsche sport exhaust is available for 2006

MIKELLIG
I would look for a year 2009 or later. The engine was completely redesigned in MY 2009 eliminating the IMS and associated problems.
so much as the best maintained, best inspection by a Porsche expert via a PPI. Owned 2, both great experiences. The pre-purchase inspection on the second told me what I needed to spend and it wasn't cheap to get it completely into the condition I wanted it to be for confidence. 90K service (most comprehensive), alignment, tires, brakes. Everything proactive I could think of by a shop that was a Porsche specializing shop that preped cars for racing. 6 years later it had needed little beyond another set of tires, brake fluid flush, battery, filters and oil changes. Oops, an O2 sensor. The expert found things I wouldn't have and I had a Previous Boxster.

Find a well recommended mechanic first and they can frequently lead you to a car they know the history and condition of.

Buy good and you increase your chances of being happy.

Look for a car owned by a fanatic. Tell from their enthusiasm in describing the car. Know the reason they are selling and verify the reason. Then PPI. Trust but verify.
Keep on the lookout for a special situation. These cars are very low volume vehicles and the rules need to be modified to take that into account. Decide if you are looking for a manual or PDK and use that as a filter for your search. In my own case, I found the Boxster I was looking for and bought it sight unseen. It was a car coming off lease and I bought it before it was turned in to the dealer. There was a year left on the 4 year factory warranty, and the car was driven by a nice lady who used it for social engagements around town. My own predjudices come into play here. Single owner with all service records, with all service performed by a Porsche dealer, are very important factors that I found helpful.
I'm in the 2010 camp. In 2009, they designed the IMS out of the engine, but that year, only the 911s got Direct Fuel Injection. In 2010, Boxsters also got DFI. Plus, Porsche was still independent, so not a VW.
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