Poor Skelly

[Dmdork]

The warrior hobgoblin leader goes down, plate mail and all. I, Zook the necromancer cast Dance Macabre and raise him as a Skelly. Would he still have his plate mail when he is raised? How would that play out? Could he even get up with that heavy armor and Skelly str? And would Skelly be proficient?

[Hellpyre]

The stat block implies that skeletons can be equipped with armor. Animate dead seems to imply that a raised skeleton doesn't share proficiencies it had in life, so I'd rule it was wearing plate but not proficient in it if the player wanted to keep the armor on it.

[Dmdork]

This begs other questions. A Skelly raised has armor scraps, a short bow and a short sword. When I raise a villager with a pitch fork, is that all he's got?

[stoutstien]

This begs other questions. A Skelly raised has armor scraps, a short bow and a short sword. When I raise a villager with a pitch fork, is that all he's got?

Up to DM. Nothing about equipment or proficiencies are locked with NPCs so it entirely DM fiat.
Skeletons also have a part in there background text that addresses this as well.

[Unoriginal]

This begs other questions. A Skelly raised has armor scraps, a short bow and a short sword. When I raise a villager with a pitch fork, is that all he's got?

Animate Dead doesn't create equipment for your skeleton. But if you have a short bow and a short sword the skeleton can use them, as they're proficient in those weapons.

Equipping an undead squad can be quite costly.

[Mr Adventurer]

Animate Dead can only make skeletons out of skeletons, so it's possible that any superior equipment has by now corroded. Danse Macabre still has the problem though.

[Greywander]

Animate dead seems to imply that a raised skeleton doesn't share proficiencies it had in life,
I don't see anything in the description of Animate Dead that would indicate this. IIRC, the lore behind skeletons and zombies is that they have the animating spirit of the deceased, but not their soul. The animating spirit, in addition to animating the corpse, also holds that person's memories, which is why some undead will mimic the actions they did in life, e.g. doing chores, patrolling, etc., mostly routine tasks that were repeated often. Although they retain memories, without a soul they are unable to learn new information, so they are essentially a mindless automaton with the knowledge and memories of that person. Coincidentally, using Speak with Dead also summons up the person's animating spirit, but not their soul, so they can answer questions from memory, but you can't pass a message along to them in the afterlife.

Under this interpretation, it would make sense that the skeleton would retain whatever proficiencies they had in life, but be incapable of learning any new proficiencies or gaining any class levels. This might also mean that skeleton mages might retain knowledge of spellcasting, though with their decreased mental state they might not have the same ability at casting spells, if they're still able to at all. Perhaps a rule of thumb might be that they lose half their caster levels.

At the end of the day, it's simpler to just use the skeleton stat block as-is. However, I think it's more interesting if we use the deceased creature's stat block with a skeleton template applied over it. This does make necromancers quite a bit stronger, but it also greatly incentivizes them to seek out the corpses of powerful creatures, and to keep them upright (a dead undead might not be allowed to be reanimated again, depending on the DM). Basically, it adds a mechanical incentive to act out their RP motives. What's that? You say a powerful knight is buried here? It would be a shame if someone were to... disturb him. And of course if you violate that grave, someone's going to be mad about it, so there would be RP consequences. If the DM doesn't like you having a powerful skeletal knight, he has ample reasons to send NPCs after you to return the knight to their eternal rest. Which, to me, is so much better than just treating it like any other generic skeleton.

[Chugger]

Animate Dead can only make skeletons out of skeletons, so it's possible that any superior equipment has by now corroded. Danse Macabre still has the problem though.

Not hard to convert a corpse into a "pile of bone" and summon a skeleton. If you already have an undead servant, have it do the work - maybe prestidigitation - possibly other spells - unseen servant. Or just have your char do it himself w/ a knife. They don't have to be pure bone or old bone - if the bones have some scraps of meat still on them, they should be convertible to a skeleton with Animate Dead.

[Sigreid]

I think the MM just lists a baseline equipment for equipment using mobs to keep you from having to figure out what masses of critters have. I don't think it was ever meant to be a limiter.