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I just began my search for a Boxster about a month ago but I'd like to chime in because I am/was in a similar position to the original poster.
The IMS is a ticking time bomb ready to go off at any moment... well that was the impression I got as I began looking for a Boxster. As others said, if that will be your feeling every time you turn the key then do an IMS upgrade. Of course it's not a 100% guarantee but should alleviate the feeling.
As I've been looking, I settled into the following choices within my budget:
Dual Row 97-99 model
Single Row 2000-2004 with confirmed IMS upgrade performed
Single Row 2005-2008, preferably with some history or IMS upgrade
I eliminated the potential for a dual row early 2000 because it would be basically impossible for me validate.
Now funny enough I fall somewhat into this category " as these cars become cheaper , the Miata-budget guys buy them and think ' Wow cheap Porsche +German Engineering - must be a deal ,right ?' .Those guys have no clue how expensive the M96 can be..."
I own 3 Miatas currently. They are rock solid and my search for a Boxster started with a search for a newer Miata daily driver for myself. A 986 is running much cheaper than a 2006+ Miata, and cheaper than many 2001-2005 Miatas, but the driving experience is night and day unless you have a well sorted Miata, of which my autocross Miata is but my daily drivers are not. I prefer the 99-2005 Miata generation but the interior is dated and feels much older to me. The 2006-2015 Miatas are nice "cars" but feel like a ford on wheels.
However I've done my research and understand not just the reliability but the cost of maintenance I'll be getting in to. I do a lot of my own work but also know there are things that will be beyond my capability, and those won't come cheap. Even silly things like getting that second key. (ugh)
Just last night I confirmed the deal, my first Boxster - a 2005 model that was well cared for cosmetically but had an engine failure at 75,000. It has been replaced with a 49,000 mile engine where the IMS has been inspected, the seal removed, but has not been upgraded. (which of course on this generation requires cases to be split).
The IMS will concern me a little, but I know what I'm getting in to.
I was looking at a fair deal on a 98 with 46,000 miles but no upgraded IMS. I was leaning toward that but prefer the one I am getting for several reasons. Personally I would have paid for upgrading the IMS on any pre 2005 model just for peace of mind. Of course its not the sole contributor to failure on the car and there are no guarantees, but its a mental thing.
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