Seeing commercials for insurance on TV.

Every time someone buys a book from Amazon.

Also every time Trump calls someone a loser.

^^^ It isn’t “loser.” It’s LEW-ZAH.

Are you thinking of that old puzzle that asks if you’d rather be given a million dollars or start with a penny and have the amount doubled every day for a month?

There are various versions of this. The one I first heard involved a kid asking his father to do the doubled-penny thing for one month instead of giving him his regular allowance. The father agreed—until he found out that it was going to cost him more than $5 million.

“I wish I had a dollar for every time I spent a dollar, because then, yahoo!, I’d have all my money back.”
Jack Handey

I would be rich every time someone asks, ” if you get a dime or a penny every time it happens you’ll be rich by now”.

I think the OP is asking each of us to say which specific thing would make us individual Jellies rich if we see it or hear it too many times, and then put that thing into the sentence like this:

If I had a dime for every time I saw one of those electric scooters abandoned in the middle of the sidewalk, I’d be rich.

If I had a dime for every time I heard a Republican say that they don’t see any evidence that Donald Trump has committed a crime, I’d be rich.

If I had a dime for every time one of my favorite shows got canceled after only one season, I’d be rich.

If I had a dime for every time a telemarketer called my house, I’d be rich.

If I had a dime for every time I heard an American say that they don’t like politics, I’d be rich.

If I had a dime for every time I saw some jackass weaving or tailgating on the freeway, I’d be rich.

^^I’d be rich as well same as with your second one. : )

It’s time to make some party prep’s at the mansion. ;-)

People yakking on or just holding their phones while driving.