Targeting is possible, but incurs disadvantage

My rule:

Making a called shot, or targeting a specific body part or spot, incurs disadvantage on the attack roll. If an attack does not require an attack roll to hit, it cannot hit a specific target. (Exception: Magic Missile never misses)

Rationale

Sometimes, your players want to hit something specific. The lock on a door across the room. One of the roper's tentacles. A dragon's wing. The apple on an NPC's head. Not a problem, but you will need to make the attack at disadvantage. If you roll well enough, you succeed. If not, too bad, you miss the whole thing.

Why would someone want to take disadvantage to do this? Two possibilities occur to me. First, to make an awesome attack! "I attack the troll and try to hit him right in the nose!" Whatevs. You be you. But the second reason makes more sense: you wish to disable a specific thing, be it that lock, or to keep a dragon from flying, or to reduce the number of tentacles attacking you. Those seem worthwhile.

But difficult. So, disadvantage.

There follow some questions, of course.

If you hit the thing, how is damage recorded? If it's something discreet, like a lock, or the gem in an animated statue's head, that thing takes damage. There are rules for how things take damage. (DMG Objects rule on DDB ($ required))

But what about in the case of a tentacle, or a wing? The Angry GM has a long discourse about this, including and extending to new monster stat blocks that include broken out hit points by body part. That's fine if you like uber complicated D&D, but I don't. So, instead, I'll keep track of hit points for the creature as a whole, but also the hit points on targeted limbs, etc., and I'll decide when it becomes incapacitated. It'll be a bit loose and fancy free, a DM fiat sort of thing. You'll have to live with it!

Arguments against

The DM fiat approach begs the question. Why not just let the DM narrate the injuries? When a dragon is at half its hit points, maybe it's just too wounded to fly anymore. Sure, but that takes agency away from the players, if they want to target something. I think that's cool, and totally in line with the heroic nature of characters in D&D. And if I'm allowing them to target something, then there should be some benefit to it, not just regular damage.

Examples

Trying to dismember a multipart monster:

Ropers have 93 hp (give or take) and four tendrils plus a bite. The characters decide to try to attack the tendrils, to cut one or more off so it can't make as many attacks. The picture of the roper shows the tendrils are a pretty small part of its bulk, so they shouldn't be a quarter of it's hit points, but honestly, without tendrils a roper is just a bitey (if mobile) stalactite. So it should be a challenge. I would give each tendril 15 hp. Somewhere between a goblin and a goblin boss. If the players want to take attacks at disadvantage, they can try to damage each tendril (I'll have to keep track of them individually). It might go well for them. It might not. But it'll be cool when the barbarian cleaves a tentacle off with one mighty swing of his great axe!

Trying to disable a monster's ability:

The party is in a fight with a dragon. It is attacking a castle, and they are on the walls. It is making flybys, frightening the castle soldiers and occasionally raking the walls with its breath weapon, but staying out of reach. The players think at it with their arrows, but are not making much headway. So they decide to try to shred its wings. The dragon (say an adult red) has 256 hp, and an AC of 19. The wings are pretty big, but a dragon is surely aware of this as a possible weakness, so it's keen on protecting them, so disadvantage still stands for targeting them. But the wings aren't going to be a really significant part of the dragon's hp. I mean, shred the wing, and the thing is still pretty strong, no? Now, if they were trying to cut off a wing, sure, that would hurt a dragon. But then also, putting a hole in the wing sail (as it were) won't immediately impede the ability to fly. After all, an arrow through a boat's sail won't really cut its speed. Chain shot, or 100 arrows, or Scorching Ray, that might do some damage.

I'd rule thusly. Dragon, 256 hp. Cutting a wing off, disadvantage, and each wing has 40 hp. Shredding the wing membrane, disadvantage, and it has resistance to piercing damage (as well as the red dragon's immunity to fire damage).

Breaking an object:

So, let's take the lock on the door from earlier. If the party is right in front of the door, they can just batter the lock. I'm not going to make them target it. There are simple rules for using strength to overcome a lock's DC. But if they are, say, across a room, using arrows to try to bust a lock that will let an owlebear out to ravage the guards in the room, then they need to target it. Disadvtange to hit, and since it is a metal lock, AC 19, and 5 hp (per the Object rules)

Attacks that won't work, and Magic Missile:

So, the rules says it only applies if the attack requires a roll to hit. So, you can't target with a Fireball. That makes sense. You can't target with a Sleep spell. But you also can't target with Sacred Flame (hits unless something saves). That makes a certain amount of sense, since it is a one-target area effect spell. They dodge, you miss. You obviously can't target with a psychic damage spell, duh. Unless you're doing brain surgery, I guess. But there's one spell that defies this simple logic. Can you target with Magic Missile? The rules say it doesn't miss. (DDB Basic rules) And that's totally the aura of MM, right? It never misses. So... sure, I think you can target with MM. It's a loophole, but a fun one. Thank goodness it takes a spell slot.

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