Gosh. People really can't figure it out huh? or maybe they just don't want to?
This is more for Yoke's sake than Simon. Regardless of what people might think or say (with the mindset that this is supposedly giving a "nice shade" to Simon) this is wholly for Yoke.
The flashback gives a context as to why Yoke still sees Simon (even a little bit) as a friend. In honor of that childhood memory and the person Simon used to be.
This culminates all of his interaction with Simon and his former party. Why he still listens to Simon when he talks and not just brush him off. Why he still tries (in a way) to help him be a better leader. It is in honor of the memories and the person Simon used to be.
People change. That is a fact. From heinous monsters that seek redemption for black crimes.... to Children with grand dreams that gets corrupted and malignant when faced with reality and growing into an unfortunate adult.
It is not to excuse as to what is done or give light to the atrocities made. What is bad is bad. But to just fully paint it black without understanding what is being painted on is just a disservice to its history.
This is not to "redeem" Simon. As pointed out, this is essentially putting Simon into a Coma. Irresponsive flesh that will continue to grow and grow without a will anymore. Some might say its a fate worse than death. That is up for each person to judge.
All this does is to free Yoke from the shackles of the past. From a person like Yoke, I'm sure at the back of his mind, he still worries/cares for some level for those who he was part of before. Heck, the fact that he's diving into the dungeon once again for Jamie shows that this is true. At some level, he still considers them "friends". Bad friends to be sure, but still "friends".
That is just how he is. It is part of his character. He wouldn't be this caring/close to Clover if he isn't. It is a core part of who he is.
Maybe it's the writer in me. Or maybe it really is just people willingly not seeing things beyond what is offered at the surface (heck, this is how it is most of the time lol). This is what you'd call character progression. Not for Simon, but for Yoke. Treat it as a way to show the MC's depth on his devotion to what he considers "friends" while also closing a grim chapter on his life. With this, he can fully move on and forward with "Clover" with nothing that will shackle him down from his past.
In terms of writing, it is not bad at all.
Edit (more thoughts): Considering the hate that Simon got, isn't it a testament to writing that such an unlikeable character was used in a way where it continues to progress the MC? Simon is made to be a very hated character. Unlike other stories tho, he is fully utilized and still had a profound impact that still drives the MC and supporting cast forward in growth. Until the end, the character is used and squeezed and dried up to its very last drop to ensure all potential use is done and over with. The end Simon deserved? Remember, he is not "fully dead". He ain't going into that hinted "cycle of reincarnation". Not all there anymore but his body is still there, constantly regenerating and breaking down due to the spell Yoke used.
I mean, if Simon (and gang) is just used as comedic relief or a low impact "Oh right, they exist" type of pebbles in the road, then there will be some that will lament the "wasted potential". It will also leave them as "ineffective antagonist" that will not have the impact that they have because giving them such a role will trust them further than what is planned for them.
Hate him all you want (he's trash imo) but understanding things is also something peeps needs to do.