Interesting observations on key wear and ignition cylinder wear. I have a 2000 so it has an immobilizer; but, other than that I think the key and cylinder mechanism is very similar to the earlier cars. When I purchased the car, it came with two keys. The valet and learning keys were AWOL and I expect that one of the keys, the one with the silver logo, is actually a later duplicate made by a previous owner. I say this because not only is the logo color different; but, the key is much less worn and has the T5 marking typically found on blanks.
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The interesting thing is that despite the fact that some of the bittings on the red logo key are completely or close to completely worn off, the key works satisfactorily in all cylinder locations. My car has roughly 73,000 miles on it so it probably qualifies as having moderate usage. The silver key is the one I use regularly. It might be a little smoother operating; but, not obviously so.
When I got the car in 2011, I installed keyless entry so the door cylinders have not been operated in the last 8 years and I expect that the passenger door lock cylinder has probably been operated less than 100 times in the cars life, so it should have almost no wear. Since both keys work just fine in the passenger door it is not like cylinder wear is allowing the use of the worn key. This leaves me wondering if there is a lot of tolerance built into the lock cylinders. If this is the case it would raise the question as to whether the cylinders can be operated with T5 keys with similar; but, not exact bittings. If so, I am happy that I have an immobilizer key because I then have a second authentication that the key is matched to the car.
My observations may be relevant to the OP because my experience with NSX key wear suggests that key wear might not be a cause of his problem. However, my experience is just a single data point and as such is definitely not conclusive.
Despite the missing keys, the previous owners of my car did manage to hang on to the key tag so I did have another spare key cut and cloned with the cut being made from the tag numbers.