Slap a DC on it. Player makes one check. Pass or fail: DM describes a montage. Player feels like the Predator or gets caught. Game moves on. I can see no situation when 50 checks is fun.
Well no, it's obviously not intended to be fun. The DM who employs a tactic like this really doesn't want Stealth to succeed. That was the whole point of my post- Stealth tends to be less pass/fail and more "does the DM want it to function in this circumstance" (in my experience).
Stealth has many hoops to jump through to begin with, and thus can easily be rendered pointless by any DM who doesn't want it be an option. I often don't bother to be proficient with it, because it's so rarely functioned. I still recall my very first AD&D Thief, trying to sneak about and gather intel on our enemies, being told that I was automatically spotted by an orc, because orcs have infravision, and the book says I can only hide from infravision "only if some heat producing light source is near to the creature or to the thief attempting to so hide....". Yes because carrying around a torch while sneaking makes perfect sense, lol.
And again, ask yourself how many standard D&D monsters who lurk in dungeons have infravision (or some other stealth-foiling sense). So here you have an ability in a game called "Dungeons & Dragons" that typically neither works in Dungeons or against Dragons, lol.
So yeah. I've learned that stealth only works when the DM wants it to, the fiddly rules are simply there to justify them not wanting it to.
In the current edition, it's even worse in some ways, as I've encountered several DM's who like to make group checks to see if the party can sneak about without being detected. Given that most armor users have disadvantage on this check (and armor users tend not to be trained in Stealth or have particularly high Dexterity in the first place), the chances of success in your standard Fighter/Cleric/Wizard/Rogue party is fairly slim in such cases.
In fact, one of the best ways to get Stealth to function at all in this edition is Pass Without Trace. A spell. Something a Rogue doesn't have access to natively, let alone Invisibility. Not long ago, I was in another thread complaining about how useless Stealth is (with regards to AD&D Backstab) when someone was like "what? in my campaign Thieves were backstabbing all the time!".
I bring up the extremely restrictive rules for setting up a Backstab in the first place, and his response was (as near as I can recall), "oh well, I always give Thieves a Ring of Invisibility". LOL.
Now I know some people are going to say "well in my campaign, I allow Rogues to..." and that's great. I'm sure there are many sane DM's have long since made rulings about stealth that actually allow it to work. But of all the skills in the game, there is none more restrictive than the ability to creep up on someone unseen.
I recently started playing Baldur's Gate 3, and I was surprised at how easy sneaking about is. All you need to do is stay out of the enemy perception range and you're hidden. The game only makes you roll if you actually blunder
into said range. And there are several ways to distract enemies to make sneaking about easier. It functions so simply that I'm stunned that it's always been so complicated at the table, almost as if the designers
don't want stealth to function!