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But, you do. This is exactly the same process that you use. You choose to have an event occur (or rather the dice choose for you) and you then backfill the scene and the narrative to make that event fit into whatever is going on in the game. There is no difference here. You keep trying to...

And there we have it perfectly laid out. The encounter is rolled FIRST. THEN the scene is created to make the encounter flow in the fiction of the game. The ONLY reason that this area has tall grass is so the DM can justify the ambush. Or, the ground will be soft enough to dig holes to...

For the players maybe. But, for the DM? Seriously?

That's the thing. There is no difference. The "random encounter roll" is not connected to anything other than, as you say, having this encounter. It's circular. It's not connected to the game world. It's not connected to anything the PC's are doing. No matter what the PC's are doing, at 6...

This could easily be true. The PC's spot the ambush because the grass wasn't long enough. They succeed on their perception check, so, now the grass is not long enough to hide the ambushers.

No. It absolutely does suddenly change height. You describe it as some grass over there and nothing else. That means that the players have a very incomplete view of the scene. That the grass might be long enough for someone to hide in is absolutely something that adventurers traveling...

Oh, come on. The ONLY reason the grass suddenly becomes long is because of the ambush, not the other way around. The DM wouldn't have even bothered describing the grass until the encounter occurred. Let's not pretend otherwise. Do you seriously describe the length of grass every single minute...

And, thus we keep up the pretense. Ask yourself this. Why did that group of monsters just happen to meet the party at that point in time at that location? It was all randomly generated. There is absolutely no difference between deciding that one completely arbitrary random roll results in an...

Your wandering monsters magically teleport to whatever location the party happens to be at the arbitrarily determined time span. The scene arbitrarily manifests itself to fit whatever the completely arbitrarily determined event has been created. There is no difference.

The tall grass ambush is a perfect example. The question that needs to be asked is, "Why is the grass tall?" After all, it wasn't described as particularly tall until the ambush occurred. The players had no chance to react to the idea that something might be hidden in tall grass until the...

Just like there might be a cook in the room?

So, to put it another way, there is no actual difference. The only difference is how well we can cover over the fact that the material is created based on nothing more than completely arbitrary reasons which have nothing to do with the players or the game world whatsoever. It's simply a...

Except that it's pretty close most of the time. That's why we have fairly flat bonuses. Most of the d20 tests that you make in 5e D&D will be roughly in the neighbourhood of 60%.

You've never made a group check? That's 4 or 5 rolls right there? You've never had the group climb something? You've never had any effect that forced everyone to make a check? You've never had something try to sneak up on the party? You've never had the group make perception checks? Right...

I will guarantee that that is not true. I know that for a fact. In any situation which calls for multiple skill checks in your games, your players fail far more often than they succeed. I know that without even sitting at your table, and, I guarantee that if you were to track it for the next...

This is something I've REALLY struggled with both as a DM and trying to get players on board with this idea. The notion that because Player A failed a check, something bad happens to Player B is very hard for a lot of players to wrap their heads around. Getting them into the habit of spreading...

True, I've never played in your game, but, by your admission, they are failing fairly often. The idea that there is only challenge in failure is one that is so incredibly ingrained in the hobby that it's almost a truism. And it's incredibly toxic. It permeates so much of play and is the...

One of the absolute best pieces of DMing advice I ever took from a module (and I have no idea what module this came from, it was too long ago) was, "So long as the players come up with some sort of plan, they succeed. Don't worry too much about the details. It's far more interesting to see...

Except in your examples, you simply piled on yet more skill checks, the failure of which will result in total failure - the vase gets dropped, the guards get woken up, whatever. Sure, you added an extra step. Doesn't really matter. The players will still almost assuredly fail. If you...

And thank you for so eloquently highlighting my point. Three separate checks to get through a kitchen, multiplied by each PC and any failure = they are heard and bad things happen. The odds of them successfully navigating this are pretty much zero.