Too long of an answer:

So that is hard for me to pinpoint, just because there's close to 900 episodes now and I think I started listening in like 2019ish? The show started in 2017 and I remember after I listened for a few weeks I decided to start from the beginning and was surprised by how different the feeling of their approach was. I would say by 2019 they we're much less willing to write off gross stuff and were more concerned with Alex providing cover for extremist patriot guests. Post election and J6 they are pretty on the nose about calling out what they perceive as Alex's more deep seeded motives. With the final form of just general disgust and every info wars episode being a new low probably arising around the 2022 sandy hook defamation trial in Texas. Maybe a little before that. I'd say that the change in perception very much follows the arch and evolution of not only Alex, but much of the country letting the mask slip. So yeah, I'd say it's gradual.

As I recall the show was always a mixture of both current info wars episodes and past ones that Dan found interesting or silly. Sometimes what they covered would be dictated by how interesting (or not) the current info wars episodes were and then over the last maybe 2 years they would go to older episodes when Alex was in "time out." Which is basically when hes on such a horrible rip of racist, xenophobic, homophobic, incendiary garbage that Dan doesn't want to listen or give it air on their show. More recently though they cover that stuff when it comes out. So I'd say he's put mental health aside and feels more of a need to document some of these things to the audience. It's really horrible stuff and you can see pieces of the through line that led this guys mental state and the murders.

Alex's shtick of being "beyond the left right paradigm" and masquerading around as some libertarian with secret truths probably mostly ended around 2019-2020 where he got increasingly dependent upon drawing in more audience solely do to his support of Trump. He also has Stuart Rhodes, Roger Stone and Michael Flynn on a bunch in that time frame. So tying those worlds together was very lucrative for him with the level of access he was getting to people Trump was pardoning and putting reliance on. I think that's the best way to look at his increasing influence and role from 2016 on. It always mirrors where the right is going because he wants a cut of the cultist grift and then will amplify deceptions to create new market space and solidify his position as someone with secret knowledge. This ebb and flow cycle creates a feedback loop and this guy who is just making up shit to sell garbage supplements is eventually selling insurrection. Recently it shows itself even more clearly. Alex goes on 5 minute tantrums saying REAL gross stuff, and it's just him trying to get a racist or homophobic clip to go viral out of desperation for money.

Go listen to the Project Camelot episodes about space raptors if you want some more zany fun stuff. It's also absolutely worth listening to their episodes covering the Sandy Hook cases (especially the ones called formulaic objections) and the debriefs they do with Mark Bankston (who is the prosecuting attorney and a listener.) It gives excellent perspective to hear Alex in front of a court and how he turns on and off without control.

It just hit Dan that what Alex is doing isn't funny but dangerous. It was episode 174 where Dan has his realization that Alex has always been super racist and how that affects the things Alex says and does.

When the show started they covered current broadcasts. Soon after they started doing regular time travel episodes where they would put Alex in 'time out' and cover a past episode. Episode 174 is one of those episodes. It's the juxtaposition between the two times that put it all in focus for Dan. If you are looking for best episodes to go back and listen to, 174 is near the top and really addresses your questions.