"Even very smart people can make stupid mistakes." All too true, especially if they're blinded by their hubris and/or greed.

"The power to give and take... could've been the kindest in the whole world.”

He also has extreme tunnel vision. Because he wants his brother's quirk. Because it's the only one he can't just steal like the others that he has at his disposal, and he doesn't see his brother as a person, he sees his brother as a possession, something for him to have, but not to care for and that is the reason why he doesn't act completely intelligently all the time. Because in his mind  He wants something that was stolen from him back.Because he thinks that's what one for all is that it's a possession of his that should always have been his that everything is his , because he has the power to take it

Just for that, I'm giving you the Windex Bottle head Quirk.

The reason why afo is implied not to have regeneration, at least in my interpretation is actually that he does have it but because hes hundreds of years old and his body has had to withstand the strain of hundreds of quirks it wasn't built for all those years (dabi shows us how crippling not having a body made for your quirks can be) and the damage all might inflicted on him, his regeneration quirks are straining and always active just to keep him alive. He needed quirks that boost the quality of healing not one that hastens it.

0:19 he’s very stupid when it matters but I must defend the transfer plan

It’s showed explicitly he CANNOT steal one for all. He molded Shigaraki to be with such hatred and loathing that he’d have the will power to overwhelm the combined consciences of all the past users.

10:05 he flat out admits he fears this quirk even more than one for all. I think that speaks for itself.

He needed the boy so that he could overcome one for all's collective will

The thumbnail looks like he made a callout post on him.

I see one glaring issue with your Overhaul fix. Whenever Kai Chisaki (sorry, if I misspelled) uses Overhaul, to my memory, he never used it on his torso or his face. He always kept those parts of his body untouched, likely because using it there would obliterate his vital organs and he'd need to cognitively reconstruct them. Even if it's for a millisecond, the pain of losing a vital organ can either break your concentration or as shown in the animé, there's a split second of shock before the person hit by overhaul realizes what happened, and panic ensues.

So if AFO used Overhaul on himself, he'd have to: have someone else use it on him, do a 50/50 coin flip that he can deconstruct and reconstruct his entire body with the span of a thought, or METICULOUSLY deconstruct and reconstruct his body one bit at a time to keep mental awareness and focus.

Am I getting anywhere with this?

There is actually a reason why he didn't take Overhaul during the prison break

"You're quirk factor is festering" he says to Hawks, as All for One trakes Fierce Wings and they grow only to the same length as Hawks damaged ones. This means that AFO would get a useless Overhaul, since the quirk factor is in Kai's arms, which are gone

Basically, AFO is stupid for not keeping a copy, or just taking it earlier, but he isn't stupid for not taking it at Tartarus

Damage to a quirk stays during the stealing process, which is why Hawk's quirk was still damaged when AFO took it

1:42 So what the doctor was looking for was "Restoration." As it will restore him back to what he was before.

10:53 He could have stolen Aizawas quirk and the quirk that Hawks's mom had (she could telepathically control an extra pair of floating eyeballs) and then pair them together to permanently turn anyone's quirk off at a distance, especially if he paired it with another quirk that increases eyesight. He could have also paired Shojis quirk with a portal quirk to remotely steal quirks.

As a MHA fan I’m just gonna say that All for one is the most arrogant son of a bitch I seen in anime

It has been explicitly stated multiple times throughout the show that One For All CANNOT be stolen or taken by force, which is why Afo groomed and nurtured Tomura into developing a powerful burning hatred for everything in order to bypass that wall.

As for the regeneration quirks, iirc it was stated that they either didn't exist or wasn't discovered until years after All For One's battle with All Might that left the both of them severely crippled and weakened.

Afo only goes after New Order because Star and Stripes was on her way to Japan to help the Heroes and he didn't want One For All and New Order to team up, which is why he goes out of his way to try and steal it which ends up backfiring on him AND also robs the Heroes of a powerful ally which also scares the other nations from sending their own Heroes.

A lot of this can be explained away by the fact that he just didn't need it. All for ones plan is basically entirely centered around taking one for all back so he needs shigaraki to do that. Once he is defeated by all might he basically achomplished what he needed to (that being shigaraki) and his defeat allowed rapid (needed) growth for shigaraki as a vessel. And with the final battle, once again, all for one is literally planning on disposing of his orignal body anyways so quirks to sustain himself are pointless when they could be given to shigaraki. And also, the rewind pill is a million times better than anything else he could of used, because it gives him INSANE strength boosts, speed boosts, access to quirks and perfectly falls in line with his plan of disposing of his body.

And not only that, but it's very possible he ignored good quirks that could potentially make it difficult for all for one to take over shigaraki, and instead planned to get them later once shigaraki was annhilated on the inside.

My point in a nutshell is that, every good quirk, every good fix to his body is completely overshadowed by just how big of stat boost being in shigarakis body would be. (not even including the fact that he could steal one for all)

So my best explanations on why he didn’t do those things are

1. Super regeneration has a weakness. We just don’t know what it is  every quirk has some form of weakness/limitation. (Eris rewind, needs time to gather energy. Overhaul needs hands and the information on how to use it. New order needs a name and physical contact.) I think every person we see who has it has an enhanced body.shigaraki and the nomus. That and eris rewind drug put afo back to his prime state the super regeneration would only put him back to his post allmight battle  state and with his mask destroyed he would be stuck, suffocating and having to fight off all the heroes at the same time

2. Overhaul needs medical knowledge to use properly and it’s how you said afo prefers to use quirks that are easy to use and are really powerful. That and his plan was always to take shigarakis body (it’s important to remember he wasn’t just trying to get shigaraki body because it was new and powerful. It was also because that was the only way he could think of to get ofa back)
It’s also possible he didn’t want to risk messing up and killing himself  as he’s trying to fix his face and his body, he screws up for one second and he just splatter himself😅

I think afo obsession was also his dumbest reason he lost and that was just not killing the user of ofa before they had the chance to pass it or train with it

2:26 - no, i kind of agree with this. In fact, there was a 2-part episode from Dr. Who that explored this very concept. An alien medical agents starting turning people into gas mask-wearing zombies because they had NO IDEA what hunans actually looked like.

10:13
He's been chasing OFA specifically for so long because it holds an essence of his dear brother. The Quirk is an obsession of his specifically because of that and so comparing the work he does for it to other powers is flawed.

This is why you don't get complicate children, even with all the power in the world there's always ways to improve.