I love the dice.
They are an essential part of the game, and while there are diceless systems, they feel incomplete to me. The little lumps of plastic that represent the will of the gods, or the fickle meanderings of Fate itself, they enrich the experience; they belong.
And yet, there is an understanding in Old School Renaissance play that when the dice come out, it means something went wrong. As with all topics, there is no consensus about this, of course: Very many OSR players would love to see 5e mechanics like skill checks and, even more commonly, the Advantage/Disadvantage system adopted into Old School Games.
I am not a friend of this idea. There even are actual OSR game systems that have a native advantage system, but they go about it differently from 5e: They give you the express option of avoiding the roll.
To say it in the words of Maze Rats:
“Whenever possible, a PC’s actions should be resolved by its player simply describing what the character does. However, if the action is risky …. the GM may call for a danger roll. …. Danger rolls usually fail, so players should do everything they can to make risky situations less so.”
Or as Best Left Buried puts it:
“Shrewd Best Left Buried gameplay revolves around ensuring as many cases of the Upper Hand as possible to eliminate ever being Against The Odds and, if possible, eliminating chance entirely with a Trivial Stat Check.”
Even Forbidden Lands, where the playtest GM asked for rolls every step of the way and only allowed us to eat meat raw and bloody because we lacked the special cooking talent, the rules explicitly state:
“DON’T ROLL TOO OFTEN
It’s hard to succeed in the Forbidden Lands. If you lack the right gear or friends that can help you, there is a great risk of spectacular failure. With that in mind, you should never roll dice unless it is absolutely necessary. Save the dice for dramatic situations or tough challenges. In any other situation, the GM should simply allow you to perform whatever action you wish.”
Loss of Control
The fog of war and the the din of battle, that is the classic moment where there is no time to do things right and careful, and the interference of enemy action makes things highly volatile — this is why combat is the one moment where the dice rule supreme. But even combat can be slanted to claw back at least some modicum of control:
An ambush is safer than an honorable duel. A trap is safer than an ambush.
This simply means that if you fight fairly and exchange dice rolls, you may fail, you may fall, you may get hurt, get weakened, or die. If you plan thoroughly and use every means conceivable to make your task easy – trivial – you succeed without a roll, and you are fine.
To allow an element of chance is to invite Murphy’s Law.
It is often necessary, but it is not ideal.
Rolling for Skills
This mindset is reflected also in older game systems having no or very few skill numbers. You describe what you want to do, and if it is reasonable, you succeed. If it is risky, you must roll a save. If you crawl along a ledge on all fours, you look like a loser, but you succeed. If you balance along it, you must roll under your DEX. If you open the door with a stick, you are fine. If you grab the handle and touch the contact poison smeared on it, you must roll a save. Rolling means you have made a mistake.
Newer game systems (but also old game systems like GURPS) have skill lists, and if you have skill lists, you will roll more often. I buy a sword. Roll Fast-Talk or Economy. I climb a rope. Roll Climbing or Athletics. I roast a rabbit over a fire. Roll Cooking or Survival. In other words, what is assumed to be standard competence level in Old School games is a series of dice rolls in New School games.
5e Advantage and Disadvantage
In that vain, you cannot prepare enough to escape the dice roll in DnD 5e – you can only gain advantage. While Best Left Buried allows you to stack advantages from disadvantage to normal to advantage and beyond until the task succeeds just so, and Old School D&D allows you to argue that if three guys help you up the wall then you must surely make it, 5e has advantage or disadvantage, and even if twenty arguments support your advantage, it is still only advantage.
The DM may allow you to succeed just so, but that is already O5R, not 5e RAW. And thus it happens that some GMs feel they are doing something wrong when they don’t ask for a roll …
… but they are not. They are doing something right: they are rewarding thorough planning.
Because even if you love the dice:
When the dice come out, it means something went wrong.
Here is another thought about 5e Advantage. (Blog: Of Slugs and Silver)
And here you have the math behind it. (critical-hits.com)