I'm gonna be real, this was a slog to get through. Slow pace, lots of clips that don't add anything, very long runtime. IMO it could be cut to less than 20 minutes, or it might even be one of those unfortunate cases where the stream just wasn't eventful enough to be uploaded as a video.

Intro might feel better at the start. It's good, just feels like it's interrupting.
This character choice clip could be cut at 1:57. We all know what chat's gonna pick and that's where the jokes stop, the last two are irrelevent.
3:01 cut here feels off
Cuts in general are slow. I think for a stream like this, you need to quicken the pace.
5:43 CONTROVERSIAL OPINION this voting for spell bit can be cut. His reactions are dramatic but in the grand scheme, he just got a setting wrong, nothing crazy happens.
9:28 this might need context, doesn't make sense if you haven't watched the right video
12:31 OPINION maybe I'm missing something, this is a very long clip where nothing seems to happen.
Same goes for the clips right after, all the bloodfist stuff. Does it add anything? Does knowing he has this item make it funnier or set something important up?
I feel this way about a lot of the clips from this point out, but feels like a dick move to list all of them.
17:43 audio blip between clips
24:00 could do with a little audio fade.
When he's describing the wallet, it's a black screen with several big gaps of silence. I personally don't think the wallet stuff is worth keeping, but if it does stay, the silence could be cut out seemlessly and you could have the mountains on screen.
Pissing Perry can stay
28:38 18 seconds of silence
The Duriel boss is fun but could still be trimmed down.

Title suggestions:
Choose Your Own Diablo 2

Thumbnail Suggestion:
Man at crossroads, one road leads to Diablo, gold, victory. The other leads to funny skeleton. https://media.gettyimages.com/photos/spoilt-for-choices-picture-id501601187

Intro suggestion (though current intro works fine)
https://youtu.be/rUHXvyJMpfc?t=127 a version without subtitles. From "Will you do what tell you to?" to "I swear". Got Tommy Lee Jones nearly dying and being controlled by someone else.