We have historical examples of crossbow use by mounted knights during the crusades that were almost certainly cocked and loaded before they got in the saddle.
This is not a rule. D&D is not a simulation of the crusades.
The Ammunition rule relevantly states: "You can use a weapon that has the Ammunition property to make a ranged attack only if you have ammunition to fire from it. The type of ammunition required is specified with the weapon's range. Each attack expends one piece of ammunition. Drawing the ammunition is part of the attack (you need a free hand to load a one-handed weapon)." (Trimmed about recovering ammo).
So, you must have ammunition to fire it. The attack expends a piece of ammunition. Thus the weapon needs to be loaded at the moment you fire it. If it is already loaded, you would not need to load it, so wouldn't need the free hand. It never says you must draw ammunition nor that you must load it as part of the attack. There is certainly some time horizon over which you could pre-load it. And certainly you cannot fire it unless it is loaded. (Technically, you don't need the free hand to draw the ammunition, only to load it. So if you don't have the free hand, i guess RAW you draw it and then fail to reload. I'd just say you decline to draw ammunition in that case).
There is no allowance for preloading weapons with ammunition. Your argument is that you can do it because the rules don't say you can't. The rules don't say you can.
The rules do say you can draw the ammunition as part of the attack and part of the statement is that you must have a free hand to load it. The actual "natural language" reading is that you draw and load the ammunition each time you make an attack and there is no explicit allowance for preloading the ammunition. You draw the weapon, and it is unloaded.
Natural language: A pistol is a pistol. It can be carried loaded. The rules don't have to tell me that explicitly, the use of the word 'pistol' does. If it doesn't operate like a pistol, then its not a pistol. The rules also don't define exactly how you use a sword, but you still use a sword like its a sword.
The rules never command me to load the weapon before firing. They tell me i must spend ammo. Imply that it must be loaded when i fire it. That I draw ammo as part of the attack. And that I need a free hand to load it as part of that attack. But if I don't load it right then, I don't need the free hand, because I'm not loading it. (It doesn't say you need a free hand to operate or fire it, just that you need a free hand to load it).
(Technically, the rules never explicitly tell you it has to be loaded to fire it. They merely imply it. Natural language kicks in, and we understand pistols fire bullets and crossbows fire bolts, which must be properly loaded to be fired.)
Any DM telling me I couldn't preload a pistol is a DM I don't want to play with.
And yes, the game is a (very rough and loose) simulation. The purpose of the rules is to avoid the Cops 'n Robbers "I shot you", "No you didn't" problem. It still assumes you know what pistols, swords, shields, and etc... are and vaguely how they operate.
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Natural language: A pistol is a pistol. It can be carried loaded. The rules don't have to tell me that explicitly, the use of the word 'pistol' does. If it doesn't operate like a pistol, then its not a pistol. The rules also don't define exactly how you use a sword, but you still use a sword like its a sword.
The rules never command me to load the weapon before firing. They tell me i must spend ammo. Imply that it must be loaded when i fire it. That I draw ammo as part of the attack. And that I need a free hand to load it as part of that attack. But if I don't load it right then, I don't need the free hand, because I'm not loading it. (It doesn't say you need a free hand to operate or fire it, just that you need a free hand to load it).
(Technically, the rules never explicitly tell you it has to be loaded to fire it. They merely imply it. Natural language kicks in, and we understand pistols fire bullets and crossbows fire bolts, which must be properly loaded to be fired.)
Any DM telling me I couldn't preload a pistol is a DM I don't want to play with.
And yes, the game is a (very rough and loose) simulation. The purpose of the rules is to avoid the Cops 'n Robbers "I shot you", "No you didn't" problem. It still assumes you know what pistols, swords, shields, and etc... are and vaguely how they operate.