do they pop on well enough that this isn't an issue.
You can usually tell - if they fit properly onto the raised nubs on the rim, it shouldn't be too easy. A tight fit is indicated when a good rap with a rubber mallet (or the side of your fist) is required. If that needs to be done in a couple of places before the cover seats all around, that's even better.
Second thing is what the best way to get them off without damaging them?
When popping the hubcaps off, the biggest concern is not about damaging the cap but rather damage to the rim. I use a standard flat bar (like a Stanley Wonderbar) with a few turns of duct tape wrapped around the fulcrum point;
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The tape prevents the rim paint from being damaged as you pry the cover off the nubs.
I sandblasted my rims, primed with a light coat of Rust Reformer, applied two coats of appliance Appliance Epoxy and baked them in the oven. The surface is a hard and smooth as porcelain - and highly chip resistant. After all that - I don't want to wreck them while popping a hub cap. This shows one of my original 1986 rims:
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I would like to be able to take them off before I go so the tire guy doesn't mess them up.
All tire places have that tool recommended by glockholiday. As long as they use that tool to pop the covers, both your rims and hub caps should be safe from damage. It is basically just the same two tools that I use (rubber mallet & flat bar) combined into one.
