-In an AU where Henry frees everyone from the studio, I think that nobody would've aged while stuck in the loop. They'd be lost to time, physically unchanged within 30+ years.
-If the workers were ever set free from the loop, it's most likely Joey would be sent to a mental asylum.
-Joey made sure the deadlines were nearly impossible on purpose, because that meant that Henry would be stuck up at the studio more often then home. He hoped that if Henry was with him more than Linda, he'd eventually love him. He was wrong.
-It's rumored around the studio that Joey has tried to sexually assault Henry at least once. This rumor is true. Joey would keep Henry working in order to tire him out enough to try and do... things... but he never got far enough. He attempted this three times, two of those he was walked in on (Norman the first time and Sammy the second), and the third Henry was aware enough to know what was happening and stop him. This is one of the reasons Henry left.
-Wally comes to work in a similar state to Buddy. He has a single pair of pants and suspenders, and two shirts that he cycles through. However Wally's reason is much darker than Buddy's. Wally's father was abusive to him and kicked him out when he was only 16. Wally got the job at Joey Drew Studios for very little pay, lying on his resume that he was 18. He was homeless for awhile, secretly sleeping behind the piano, until one day Sammy got mad at him for losing his keys again, and Wally just broke down in front of him. Sammy took him in after finding that out. Soon both Thomas and Allison knew aswell, and all three swore to secrecy. Allison helped Wally to sew patches on his clothes and Thomas helped him keep track of his keys. Wally could never be more grateful to them and felt awful when he heard all three had been taken by the machine. Wally was one of the few workers to escape the ink machine, and he'd moved to Florida soon after.
-Both Henry and Wally, while escaping being turned into ink monsters, still never aged just the same as the rest of the workers. The ink has a special power to it that keeps people stuck at their current age until it's drained from their system, which is nearly impossible to do. Joey had tricked both of them at two different occasions to be injected with the ink.
-Joey secretly used to physically harm Grant on occasion.
-Bertrum's soul was not fused with the amusement park ride. He made the ride that way on purpose as a trap for Joey after he'd found out what Joey was doing. Bertrum instead became the Lost One that's shown on the balcony in Chapter 4, the one that can talk, and is quoted to say "I want to go home..." This Lost One and Bertrum share the same voice actor in the real world.
Major Trigger Warning. Stop here if you are sensitive to topics such as suicide, self harm, and gore.
-Grant tried to hang himself. He couldn't handle the stress Joey was putting on him anymore. However, just as he was going to do it, Shawn walked in on him and quickly stopped him. Shawn was able to convince him not to try it again, however Grant still harmed himself.
-Joey found out about Grants attempted suicide by unknown means, then proceeded to choke him to death with the same rope in his office. That's why the choking audio is in there. Grant tried to fight him off and had accidentally activated the tape. Joey didn't notice so the tape stayed there. He later used Grant to make Barley/Fisher, which is why Fishers head is detached.
-Joey got so fed up with Shawn drawing the Bendy dolls wrong on purpose that when he killed him he made sure to break his jaw and stab a knife into his mouth. The last thing Shawn heard was "How do you like crooked smiles now?" He was later used to create Charley/Piper, which is why Piper has a broken, crooked jaw.
-Lacie was close on Joey's trail and that's what ended up getting her killed. Joey used her to make Edgar/Striker, only to realize she was still somehow able to talk. He sewed her mouth shut.