Get a popit removal tool of some kind. Actually works much better than a screwdriver. And keep in mind that even the master techs break popits sometimes. Just get a few extra to have on hand in case.
Also, even if you are missing a few popits, things aren't going to fall off the car. The bumper is really only seriously attached to the body where the grille screws it in to the brackets. The rest is popits and clips, which will hold things in place, but won't keep the bumper on the car at 70 mph. You aren't really relying on them to keep things on anyway. I only have about 5 bumper popits left. I need to get a few more.
You're right. Suck it up and take the risk. If you break it, just replace it or live with the broken version. <-- This attitude is required if you intend to modify your car. You (or anybody else) will never get things back together as well as it was put together at the factory. Just a fact you have to live with if you want to customize things.