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There are no guarantees with a car
even a new car.
Having said that, the risk of an IMS failure is probably 1-2% per year per car. Outweighed by the 20 or so other potential failure modes that could happen. There are people who have 200k+ miles with little trouble, and others where serious replacements were needed before 10k. No way of knowing.
Having owned 2 and been following on all the Boxster forums for years, here is what I'd do.
I'd buy the car and arrange to drive it locally for a day or so at varying speeds to acquaint yourself with the car and to see if there were any out-of-hibernation failures that would crop up in the first few miles out of hibernation. I'd get the oil changed and then begin my trip. I'd have a copy of the AAA towing guide and a list of dealer locations with me (not because I think you'll need them but I'm one who likes to take reasonable and cheap precautions).
As to if you should do the IMS upgrade, I don't know your risk tolerance or ability to financially and emotionally deal with a big failure. But after all you are buying a 10 year old car and not a new econo-box with warranty so you must have some tolerance. How much to spend on preventative maintenance is always a tough question.
Hope you enjoy the new to you car.
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