Hitch would have ADORED the digital revolution, especially when it comes to CGI. He was constantly experimenting with new and different motion picture quality systems, from Vistavision to 3D. I imagine his work would be similar to that of Iñarritu or Cuaron - freed from the encumberances of a ginormous camera limited by physical space, he'd really let loose. Welles too - it would finally be cheap enough for him to get what he needed to make his work without a studio system, and people would see it - he'd be doing stuff similar to Soderbergh, making movies on his own terms with cheap equipment and getting Netflix deals and alternative distribution ideas.
I imagine Kubrick would probably be more of a camera purist (he used the outdated Mitchell BNC camera throughout his career and eschewed widescreen ratios because they didn't use the entire amount of available film stock), but who knows? Maybe he'd be like Steve Yedlin, Rian Johnson's cinematographer, whose extremely deep analysis of film vs digital is Kubrickian in its attention to detail and mastery of the technological process. Kubrick might have consulted with someone like Yedlin and then ordered custom digital cameras from a company like Red, much like Fincher did for The Social Network. Kubrick probably would have enjoyed having high speed internet and an editing workstation and dubstage in his home since he hated to travel. I also think some of the new Mandalorian/Unreal Engine virtual location tech would have been very appealing to Kubrick, who used rear projection with similar results in 2001. And he would have LOVED gimbals the same way he loved the Steadicam when it premiered. It would have been very interesting to see them all do stuff with these tools.
I don't have a very strong opinion on the show (I think it's more or less harmless) but it is a good example of how this "lofi" aesthetic they do is actually quite artificial and constructed. There is a massive team on this - they even have an OMF export and a sound mixer! - and they're packaging it aesthetically (and thematically) as some kind of homespun DIY project. I don't think it's morally wrong or anything, but it's important to understand that not all media that looks homemade/little-guy-ish actually is, and it's important to recognize when we are being sold an aesthetic that isn't necessarily reflecting reality.
Your brother Blaise is a friend of mine from film school - I saw him a few months ago when the film was in town for a festival, and the passion that he spoke about this work and your obvious passion here is for me one of the big takeaways - You guys really believe in your vision and your work, and because of that distributors want to see it. No one will care about your film more than you, so you guys are setting the bar nice and high. Congratulations on your film and your success! :)
For me the one book every film student needs to read is "On Film-making" by Alexander Mckendrick, written by the greatest film teacher of all time, filled with totally amazing ideas that even veteran filmmakers would benefit from. Most film books are crap. This one is sensational.
Honorable mention: "Directing Actors" by Judith Weston, the single best book on how to be an actors' director ever written.
Community's bottle episode was fantastic, and a great way to have that kind of episode while showing off a few tricks.
Counterpoint: I kinda get this. It's still a horrid scene, but I think what he was trying to do here is to like...have some of that banter that Han and Chewy had, arguing about little things in the midst of big things. Like when Han is repairing the Falcon and the tools fall on his head? Or anytime C3PO is saying something silly while on Chewy's back in Cloud City - those are fairly silly moments but they totally work because C3PO is meant to be comic relief, and Han is meant to be a bit rogueish and everymannish.
This doesn't work because the Jedi are supposed to be the straight characters and the jokes are supposed to be left to the normal people. Which is why it works decently well with Finn in the new trilogy, or even Rey before she is revealed to be a talented Jedi person.
There is a place for this kind of comedy in Star Wars, and I understand Lucas wanting to put some of that into his prequels, but this....does not work.