I'm posting a counter-experience, not to disagree with you, but to give hope. It's possible for things to be better, because sometimes things are better. Sometimes.
There is one parking app in Pittsburgh. Just the one. Street parking, empty lots, multi-story garages, empty grass fields. All of them are ParkMobile. The only exception is when the parking lot is a gravel field eight blocks away from the monster truck rally, which doesn't have an app at all, it has a dude with a rubber-banded stack of bills.
And, critically, there are pay stations. Again, street parking, lot, garage, whatever. Every quarter-block, big chunky physical thing the size of a payphone. On the side are app instructions and zone number, on the front is a standard-ass monochrome kiosk interface that takes cash and card.
I have repeatedly seen senior citizens from out of town figure out the pay station in a few minutes, which ain't great but it ain't terrible. The biggest source of confusion is from people expecting a physical receipt to put on the dash.
I suspect the main reason it works that way here is because most surface lots and garages are actually operated by the local government, and it's the same department that's in charge of street parking. There's probably a directive somewhere that says every parking spot must have a physical pay station within 50 feet, and it actually happens. I'm sure there's a lesson here.