Shoot your boot fitter
Um, if your boot fitter is a credible boot fitter, he will give you new boots based on an unsatisfactory fitting. After you have boot work done - especially grinding and cutting of any sort you should not ever have to touch the boot on your own. If a mistake is made the boot should be replaced or it should be corrected by the fitter. If they refuse, demand the money for the boots and take your business else where. If a boot fitter drilled in correct holes in any of my boots he would have a seriously pissed off customer on his hands.
As far as the strength of the plastic goes... it depends on the boot. I have a pair of Dobermans that i dont think i could destroy, but i skied in Salomon Course boots for three seasons a few years back and they were retired due to the cuff of the boot splitting between the second and third buckles. I didnt think that the plastic was very strong - i shouldnt be able to do that to a boot that is that stiff (i only weigh 155 lbs and am 5'7"). I found the beast to be pretty soft in the store when i had it on. It may become slightly brittle in the cold (or may not), but i would avoid putting any extra holes in it. If you realy need 5mm or so less in the upper cuff, you should look to a lower volume boot.
Later
GREG