KC, read your post quickly, but first of all, its never necessary to pump higher than max rating to "seat" a tire, there is no need and all you need to do is to make sure the tire is positioned properly and inflate tire normally, and just keeping an eye out to make sure you havent pinched the tube or that the tire wasnt centered properly on the rim.
forget this overinflation idea, its not needed.
I wouldnt trust this tire, if it was doing weird stuff before, and you over inflated it, it just aint worth it.
also, I wouldnt worry too much about cutting a tire or whatever. Sure, it can happen, but if you are riding on pavement, and you have a normal ability to look where you are riding and not run over obvious stuff or run your bike up against sharp objects, a sidewall damage that serious is pretty easy to avoid. If you are really concerned, take a spare tire, but if your tires are in great shape (always a good idea for a trip) its certainly not a necessity.
As a professional driver, you know the most important thing is being aware of what you are riding or driving over at all times, not smacking into sharp edged potholes or whatever because you arent paying attention.
the whole "booting" a tire with an American dollar bill does work great if needed, just be aware that the chances of damaging a tire like this is pretty darn low (touch wood!) but having very good quality tires from the get go to me is the most important, and to always be aware of avoiding debris.
If I happen to run over broken glass if I havent noticed it, I'll stop and take a minute to very quickly run my finger over the tire to make sure there isnt any shards stuck in the tire. Just doing this makes a huge difference, as shards can get stuck in, then over time, work their way in further, causing a flat. Totally worth the 1 minute to do this away, waaaaaaaaaaaaay less time and hassle than fixing a flat. I wet my finger, make a line on tire, then work around to make sure nothing is stuck in.
Recently had to fix a flat on my wifes bike because she ran over stuff she didnt notice, a week later a flat. Same green beer bottle glass shards she ran over the week before and at the time I asked if she ran through the bunch of it that I avoided, but she had no idea. Normally I do the tire inspection right away, but obvoiusly something came up, we were with friends, and I forgot. She never used to believe me about why I do this, but this time was a good example.