PraetorianWolfie: Thank you for sharing the file. I've given it a look.
So, as far as I can tell, this is not actually a glitch.
Spoilers follow:
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Lucy is indeed not meeting you outside the arcade, because the phonecall you received from her did not give you the option to explicitly arrange such meeting. In McCoy's KIA, I found the Lucy's phonecall recording where she does not mention meeting up at CrazyLegs' shop. Additionally, the save game data indicate that CrazyLegs Larry was offended by McCoy (McCoy drew a gun in his shop and CrazyLegs left), so this precludes meeting Lucy outside his shop.
I found rhe passage to the Kipple however to be open, and I could successfully reach the Kipple related endings that are possible in this scenario. Let me know if you need any hints as to where the passage to the Kipple can be accessed from.
ManiacMcGee: every time i try and enter through the tunnel McCoy just stands there no matter how many times I click with the Blue arrow, and while the call in the Kia doesnt say about her going to crazy legs, when the call actually happened at the beginning of the chapter she does say to meet there.
The passage to the Kipple is
not accessed from this tunnel:
https://i.imgur.com/Px0Ya5q.png McCoy will refuse to proceed on foot further into the tunnel that way. I do notice what you mention; the first time you attempt to walk down that tunnel (probably in Act 4) McCoy will in fact say "The tunnel stretched for miles. I was sure it came out somewhere, but I didn’t have time to find out." But all the subsequent times you click on the blue arrow he will just refuse to walk further without saying anything. So, technically, we could "fix" this by having him repeat the above quote, or remove the option to walk down there (the blue arrow hotspot) after McCoy says he won't do it.
For the path to the Kipple you should try going through these scenes:
https://i.imgur.com/4jPu8T8.png https://i.imgur.com/zfNP35c.png https://i.imgur.com/s9IRkVg.png About the Lucy call. You are right, she does say "I'll meet you there ok? At the place where he sells the cars." even in the case where CrazyLegs Larry is gone. It is like this in the original game code, and I'd say it is indeed a bug, since it can be misleading for the player.
When CrazyLegs is still at his shop, Lucy will say more to McCoy about her plan to escape by car.
Anyway, like I've said above Lucy won't be outside the Arcade if CrazyLarry is offended and gone.