If I remember correctly, the TIA recommendations are no more than 90m for the horizontal cabling run, allowing 5m at each end for the associated patch cabling. Sounds like your particular situation exceeds this and is pushing the Ethernet standard.
I'm assuming a TDR is being used to measure the length. Ensure that the appropriate settings are in use (nominal velocity of propagation or whatever parameters the device allows).
Regardless, you may end up in a semi-gray area technically (where two results contradict), which will likely result in an overruling and more pronounced administrative/political/business area. If I were the customer in this instance, I'd likely consider it a fail given the above (measurement well over the spec; estimate based on jacket markings likely over spec) provided there are no mitigating circumstances.
I look forward to other responses on your last question. I typically take a quite conservative approach...keeping to under the spec max distance and leaving allowances when estimating cable distance during the pre-install survey. If the distance approaches the max limit, fiber is recommended.
Best of luck!