About 10 years ago we still had two Drive-In's left in Nebraska. One was way out west in the panhandle, the other in a small town called Neligh, NE about a 2 hour drive from Omaha.
I didn't expect them to survive and wanted my kids (appx 8/9) to be able to say they've been to a Drive-in movie before they were completely gone.
When I was a kid the playground in front of the screen was very basic metal pipe stuff on dirt/grass. A metal slide, jungle gym, merry go round, etc.
The Neligh Drive-In had a couple modern inflatable bounce house/slide type stuff.
They had a 'Pajama Contest' down at the playground and my boy won that with his Spiderman jammies. He won a wiffle ball/bat combo set and some gift certificates for the concession stand. I've never seen him eat a slice of pizza with a bigger smile on his face. I just backed the pick-up in, dropped the tailgate, and put a few lawn chairs in there. The place was packed.
We really enjoyed our visit so I followed them on Facebook for a possible return trip. I remember the the Drive-In doing a fundraiser to upgrade their projector from the old film reel type to digital because movies made on film reel were being phased out. Therefore the film reel projectors would be useless for modern movies.
iirc they needed to raise $90,000 for the upgrade or they were finished. They must have raised it, because they're still open to my knowledge.
Since then a Drive-In has recently opened just outside of Omaha. I've never been to the new one and don't know how successful they are.
Drive-In's are a tough business in areas that get winter weather, because they're seasonal. They're maybe open half the year (at most).
Not to mention they're weekend (Fri-Sat) entertainment. The movie doesn't start until it's dark outside and therefore doesn't get over until near midnight or after. You're not taking the kids to the Drive-In when they've got school the next morning.