No one is ever going to convince me it wasn't a rule in the writers room that Sam always had to be more. Both on the positive side (stronger, faster, smarter, etc) and on the negative (had to had have more bad things, be seen as the one who had it worse, etc). I mean Dean goes to hell for 40 years, so Sam had to go for 100.
So I do believe they went into the finale with the mindset that Sam will suffer much worse because Dean got to go to Heaven while Sam had to carry on without him. But as usual Jensen made it about Dean, and Dean was pretty much what everyone talked about after the finale. I don't think the writers intended that.
My big issue is they they took this attitude into the finale. It's not Dean's death I had the big issue with. Even as far back as s 1 part of me felt Deans' story would end tragically. The fight with the vampires was Red Meat all over again. Sam took out 4 or 5 of them, saved Dean twice and did it all with a concussion and Dean struggled to take out 1 and was killed.
I didn't get the impression anything more than a week or two had passed since ep 19. Dabb isn't subtle. If he wanted us to know a lot of time passed, he would have made it obvious.
With the epic mess of the Chuck storyline and the shows refusal to even give Sam one line of dialogue to acknowledge Dean, does he have a legacy or not. Jensen specifically talked about this. He was worried about Dean's legacy. I've been doing a season 2 rewatch and I find myself at times, asking did this really happen? Am I really supposed to believe that Chuck started writing the story when Dean showed up at Sam's and he stopped when Sam talked Dean out of killing him in 20.17? Then the finale doesn't make sense because the brothers were never really connected or had the bond because Chuck wrote that. Chuck said Cas always rebelled but 18 tells us it was Deans' influence. But if Chuck wrote that than that means Cas rebelled because of Chuck's writing.
Covid restrictions aren't' really an excuse because they had months to make it work. If they couldn't' they had months to rework the finale. If they wanted a tragic ending for Dean, they could have had Sam call the ambulance and had Dean give 'if I don't make it speech' but after the commericals we find out Dean did but he ended up paralyzed. They could have then had the montage of Dean becoming a Sonny/Bobby like character and Sam hunting with Eileen. There are ways around this if the actress wasn't available.
IMO, the finale season would have been better if they actually did what they said. Focused on the characters rather than the the cosmic stuff. Go small. Imagine if they wrapped up the Chuck stuff in ep 10 rather than 19 and used the back half to explore who the characters were/what they wanted without the obligations. There is nothing wrong with being a hunter and I don;t get this notion that Dean had to stop hunting to be happy. He loved it before all the cosmic stuff happened.
I think Dean would have been able to let go of Sam if Sam was still in the bunker but stopped actively hunting to take a more Bobby like role.
I go back and forth on whether I want a fix it season. One one hand I really want Jensen to be in charge of Dean's fate, but on the other given the mess of ep 18 that puts any reboot in between a rock and hard place. Because if you do a reset, it erases Cas's confession or if there is something like this is Deans' coma dream and Dean doesn't return Cas's feelings then it all the drama and controversy would restart.