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Step back from the ledge. I paid $11K for a 97/Tip in Aug 2015 with 16K on the ODO. It was/is very clean and has some nice options on it. I was able to talk to the indy who had done the most recent work on it. I was satisfied. No PPI.
I have put 10K on it in 22 months. I drive it regularly and hard when I can. I have spent about $3K on needs and $800 in wants during that time. I had an indy X/O the AOS plus other stuff to the tune of $1,100 and I just put $600+ worth of tires on. I have done all of the regular maintenance myself. I have read on the forum, multiple times, to set aside a $1k a year for maintenance. How much work can you do yourself? Mine is 20+ years old also. I have had to replace both window regulators. Expensive and annoying. But it is more than worth it to me.
The 99's IMS has a +/- 2% failure rate? You are more likely to get in an accident driving it than the IMS coming unglued. I got rear ended in March in the parking lot at work by a kid texting.
If you over think it, you won't be able to enjoy it fully. Safe = Corolla. More fun than you know what to do with = Boxster. Safe travels.
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