Wild & crazy ideas, don't do any of this until someone who actually knows what they're doing chimes-in on whether they're bad ideas ... but where's the difficulty?
Are they hard to get in place, before you even try to push the pin in? If so, what about a tiny bit of dry lube, or is there a downside to using something like Vaseline, especially if you wipe excess off? I mean just on the contact surface between clip & paint, if it's hard to get it in place initally. I don't think you want to get any lube between the pin & the outer part of the clip though.
If you mean it's hard to push the pin in once the clip's in place, I'm pretty sure I used a flat ended hole-punch for my 240 clips, with a really small hammer so as not to apply too much nasty force.