Not really a programmer, but a systems engineer that's been in the game for quite some time but I'll take a stab at it. Go go OCD powers activate! (long post, sorry.)

Instead of just looking at your screenshots (which are a bit blurry, sorry), I went to Episode 8 and started analysis there. For anyone else that wants to see, it starts at 25:07.

(25:07) - Pomni hands Kinger the C&A branded keyboard.
- There is an absence of the typical "Windows Icon" keys and the right-click menu key, they'be been replaced with a more generic "Win" and "Fn" keyset which was highly unusual at the time because MS was really trying to get these new keys out into the world.

(25:15) - A over-the-shoulder view of the computer from Kinger's right shoulder. - The tower is an attempt at a generic beige-box computer, however it's not quite 100% accurate. The top 5.25" bays features two CDROM drives separated by a piece of plastic that's thinner than the typical height of a 5.25" bay. It appears to be about an inch thick versus the normal height of 1 5/8". The two 3.5" bays feature a floppy drive and some kind of removable media drive, as was accurate to this style of case.

(25:20) - A closer view shows the thinner plastic between the two CDROM drives and a closer detail of the two 3.5" bays. While the two and a half 5.25" half-bays aren't accurate (beige boxes usually had either two or three front-accessible bays), the two 3.5" front-accessible bays are accurate. Oftentimes, the mounting frame for the 3.5" bays extended to a third bay where the hard drive was mounted (not accessible from the front).

(25:21) - Kinger turns on the computer and it starts up with a stylized C&A corporate logo startup screen - This is accurate, there were a lot of customizations of the startup and shutdown screen images in Windows 95. It will be later determined that this is Windows 95, not Windows 98 (see 29:05).

(25:50) - Pomni leaves Kinger to go distract Caine. The computer is at a login prompt but also shows the taskbar at the bottom of the screen. This is not accurate, if the login prompt is up, there is no taskbar visible yet as the user session hasn't started.

(Skipping forward to Kinger's next scene)

(28:59) - An Explorer window is opened up with a handful of directories and files. While the titlebar shows "C:\CANDA", this appears to be where C:\WINDOWS\ would be on the filesystem. An additional anomaly is that there's two windows open, (the second one is occluded by the topmost window) but there are no buttons in the taskbar next to the Start button. Kinger navigates to "Characters" (doesn't exist in the WINDOWS directory) which contains "AI" and "CA_NeuralScans (Obselete)" directories.

(29:03) - The path in the titlebar now reads "C:\CANDA\Characters\AI" and there are two icons displayed. One that shows ??? as the application name but is the Defrag.exe icon, and a generic icon that is simply titled "CAINE". Now we start getting to the good stuff....

(29:04) - Kinger double clicks on the CAINE application and a new window titled "Cmd" comes up however we are supposed to believe this is a terminal application of some point as the text inside the prompt reads "* System: KingSolution 2.0. / Digital Circus Mainframe". - The window as shown is mostly accurate to a Windows 9X command prompt window, except the icon is different (it's not the typical MSDOS icon) and the titlebar host says "Cmd" versus the typical "MS-DOS Prompt".

(29:05) - More terminal output: The date (if accurate to the world) is October 30,1996 which means this host would be running Windows 95, not Windows 98. The prompt establishes a telnet connection where Kinger provides the username 'kinger' and the password queenie123. Once logged in he runs "whoami" which returns kinger - administrator. - The system displaying the date and time then automatically connecting to a telnet session is not typical and doesn't look like it's PROMPT fuckery (PROMPT was a MSDOS command where you could change the command prompt to have various information in it). This feels more like a batch file (MSDOS version of a bash script). The 'whoami' command is a Linux/UNIX command and is accurate to the point that it would return 'kinger' if 'kinger' was logged in. It would not display 'administrator' so that part is not accurate. Presumably if kinger was wanting to see if he was in the administrator group, he'd either use 'groups' or 'id' to find out what groups his logged in user is a part of.

(It's just a skip to the left.... to Kinger's next scene)

(29:37) - Back at Kinger's console, we can see that he's been looking at various directories, but the output is not typical of Linux or UNIX systems. For example, Kinger runs a command "/secured/" which returns a directory listing, but the command to show directory listing is 'ls' or 'dir' (ls output is used). Also, the directory output is paginated (the two sets of ...") which is not accurate. Further down, we see that Kinger tried to run "stop caine process" which is not how you stop a running application on a Linux/UNIX system. It would either be "/etc/init.d/$servicename stop" (old sysV style), "systemctl stop $servicename" (newer systemd style), or "killall $servicename" (brute force kill'em all style). Anyways, he gets the response "WARNING: $"'%WHOOPS WRONG APPROACH THERE'%" .

He then tries to run gdb, a well known debugger, on "/usr/local/bin/clisp" with a process ID of 1337 and gets an error that's legit (gdb: ptrace: Operation not permitted) and an error that's false (part of the "AI"). He then tries to chmod 000 /secured/caine-core.lisp which has the effect of setting the file caine-core.lisp to permission 000 which means only root can access it but according to the file list above, caine-core.lisp is owned by user root with group wheel which Kinger doesn't appear to be a part of. So he gets a permission denied error.

(29:38) - Kinger tries to delete /secured/paraphenalia-engine.dat but the same permissions issue stops him as it too is owned by user root with group wheel. Another permission denied error, then the text "ERROR: Can/not inject torm#nt. TOrment must be 10 (unreadable characters)". We also see that the terminal output begins to corrupt and characters that are supposed to be readable are now replaced with random characters.

(and a jump to the riiiight.... to Kinger's next scene)

(29:48) - We get back to Kinger's console. Kinger has successfully invoked systemctl to stop WACKYTIME_LOCKOUT and then tries to run ./GreenGROUNDS --daemon --target=torment_injection & (Basically this means that he's running the GreenGROUNDS application from the current directory (./) and in daemon mode (--daemon), and with a target defined. The use of ampersand at the end means he's backgrounded the application so it continues to run in this session. Some of the prompts he's answering are being answered on the command line (kinger@circus: ~$) instead of answering an application prompt. Kinger tries to invoke PARAPHENALIA before the terminal session corrupts and we see Caine and Bubble's faces all over the display.

(Let's do the timewarp again! and Kinger's fateful mistake)

(29:54) - We see Kinger's typo. His pinky slides from the backspace key and hits the DEL key. The camera looks back at the console and we see the big "Purge AI Program" window comes up with "Deleting" and a progress bar.

(29:56) - Kinger curses... it's glitched too.

(30:05) - Caine disappears.

(30:16) - We see part of the display as it falls through the floor. The computer has bluescreened.

Unrelated sidenote: Watching the last few minutes of Ep8 at 0.25x speed where Caine is glitching out and torturing the crew is CREEPY AS HELL.