I took a tour of the Royal Military Academy at Sandhurst in the UK (the English West Point, essentially) some years ago, and the guide showed us an old cannon that he said a group of cadets filled with explosives and tennis balls and fired years ago, I think in the 1960s, and it was played off as good fun. The tour group chuckled, and then began murmuring about how that would be turned into a much bigger deal today, how people would be arrested, etc. I've also heard stories in the military of the shenanigans that people got away with even as recently as the 90s and, I'm left thinking the same thing - man, you'd go straight to jail for that today. Beyond that, you hear stories about WWII or Vietnam vets meeting their wives while deployed, swimming in the ocean, getting into trouble on the town; meanwhile, my deployment, which was years ago, was little more than a paid prison experience. No alcohol, no mid tour leave, highly supervised MWR trips to museums or dry restaurants. You literally had to write your name on a whiteboard every time you went to the bathroom. Why does my father-in-law describe Chinooks delivering pallets of beer to them in Vietnam? Why were WWII Marines in the Pacific able to just jump into the ocean and swim around with the locals whereas today you'd practically be dragged before counter-intel officers if you wandered off base and into the ocean?
So on the simple merits of your question we can easily say "yes" it would have sucked a lot more to get in trouble in the bad old days in the service.
For instance it was only in 1862 that Flogging, like straight up being tied to the mast and whipped a few dozen times, was outlawed. And while it gradually became more restricted for its usage, there were still infractions short of mutiny or sedition that could land a sailor a meeting with the lash!
With that out of the way the question of when the DoD became the "No Fun Zone" in some respects is actually a very interesting question! And one that sometimes doesn't have a great answer, and of course every individual unit and each branch has its uniqueness, and can even vary just with the rotation of a command triad or lower level officers and NCO's.
And it also is something that I have never seen great literature on despite the question occurring and discussing it with some dear friends over the years. Though one theme that has been suggested is that it really died with the end of the draft and the birth of the All Volunteer Force. With more of a focus on long service volunteers on both sides of the E/O divide and a consistent size after the ups and downs of mobilization through the first half of the 1900's you see the shift. The force becomes less representative of the total populations, less "goof balls" and relaxed non career dudes, and more 'Try-Hard' lifers able to thrive in a shitty unit culture essentially.