My 2.5 l Duratec V6 has a relatively stiff oil dipstick that is 19 inches tip to lip, and the tube it goes into is straight. My Rogue's dipstick is 24 inches long and flimsy, which it has to be to negotiate the bends in the dipstick tube.

Is there a trick to getting the dipstick to go down without making a scraping sound at some point?

Don’t see a problem of it scraping while going down. I got ocd and I don’t think about any scraping causing any actual issues but auditory nuisance. Never really think about it if it did anyways.

Only way it could be done is if you rubberize the dipstick end but then it would melt away anyway. Just ignore the scraping sounds. Changing oil should be satisfaction enough.