Just watched, some thoughts...
Overall I enjoyed it but it was a bit too hit and miss and the pacing/flow was off.
-The opening - I actually liked it, I wish there had been more wtf moments like that.
-The best part was with the traveling Salesman. This was as close as the movie got to Pee Wee's Big Adventure.
-The bank robbing trio - There was some missed potential here. The interactions with them felt too rushed. There was no real motive for the leader to come to respect Pee Wee. In Big Adventure, Pee Wee helped Mickey get through the road block so there was a reason for Pee Wee to gain respeck. All they really needed to do was have the leader hold her switchblade to Pee Wee's throat and have him stand his ground, or he could've helped them get through a roadblock as a nod to Big Adventure.
-The Farmer's daughters - I kinda feel like they should've dropped this part and fused it with the Amish. Pee Wee should've been more panicked during the shotgun wedding and the truck ride.
-Christopher Heyerdahl ( main Amish guy ) - I have to admit to the guilty pleasure of watching Hell On Wheels ( somewhat ridiculous AMC show ), where Heyerdahl plays the main villain known as The Swede. Anyway, they really missed an opportunity to bounce Heyerdahl / Pee Wee off of each other. Maybe there could've been a buggy chase or something idk.
-Pacing - My biggest issue with the movie was pacing. There was an inorganic and rushed feeling to most of Pee Wee's encounters. I liked the trio/Amish/wildman sequences, I just wish there had been more time to actually flesh out some of these parts. They should have either nixed some of the shorter sequences or made the movie 10-15 minutes longer. Things were also a bit too light. As goofy as Big Adventure was there was also a lot of tension. Burton did the a good job of treating Pee Wee as an eccentric but somehow weirdly believable character.
-Scope - even though it was a road trip I never really got the big road trip vibe that you get from a lot of similar movies. Sure, the budget was not huge by today's standards, but I've watched movies with much smaller budgets that manage to nail having a massive feel. Looking at the budgets this had 30 Mil vs Big Adventure's 7 million. Basically Big Holiday felt too much like a series of loosely connected skits, the transitions were a big problem. The focus was too tight on Pee Wee whereas it should've given us a few scenes to reflect on the prospect of Pee Wee's character in the real world.
-Joe Manganiello - Wasn't feeling it with this guy. Although it would've been unlikely I think they should've tried to get someone like The Rock. That would've been an interesting dynamic. They overdid it with the dream sequences as well.
-The Renegades - there was no payoff for Pee Wee's band even though it was initially kind of established as something we would see resolved ( Pee Wee stomping on the rehearsal space model ). I was looking forward to seeing Pee Wee rock out.
So yeah. Even though it seems like I'm really dumping on the movie I didn't hate it. I still feel like Pee Wee / Reubens is strong enough to carry a film as the focal point / titular character, this movie was more so let down by the directing.