I'm a firm believer in that you make you own luck  I will do the things that give me peace of mind (within reason and budget), and for the rest, just enjoy!
Obviously, I would do the IMS bearing upgrade first, but M96-97 engines have some pretty serious issues with engine oil starvation if you push them hard... start with the right oil, oil quantity, oil filter, oil sump baffles, maybe a deep sump and an Accusump. There are other more expensive things you can do like dual scavenge pumps, and even a dry sump upgrade (if you have the money or skills). Oil pressure and temperature gauges will help some, but a real data logger would be best since your focus on the track should be outside not inside.
It all depends on your driving skill level, what you want to do with your car (track only or track/daily driver), and off course your budget.
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2002 Boxster S - NHP 200 Cell Headers,test pipes,Borla CatBack,Competition Plenum,74 mm TB, EVOMS Tune,Tarett UDP,Eibach Swaybars,BIlstein PSS9s,TuneRS rear toe links,wheel studs,15 mm wheel spacers on all 4,EBC yellow stuff pads,Sebro rotors, EBS oil baffles,160 deg Thermostat,2 quart Accusump,full filtration remote oil filter,rad fan switch,custom gauge/switch plate, Race Capture data logging, 90K miles
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