By RAW you cannot trade off anything that is a prerequisite for something you have, so I'd be surprised if you can trade off any of the wizard levels via the encroaching darkness mechanic.
Also, the point wasn't to go into dips to enter the classes, the goal here was to use just Shadowcaster/Warlock and enter a PrC that way. I realize there are ways to cheese yourself into PrC's with spellcasting requirements, I've seen hundreds of builds that do it, that's not what I'm trying to do. I'd actually like to see a PrC that was made with the intent of combining Shadowcaster and Warlock, not just a "progresses both classes" PrC. Kind of like how the Eldritch Theurge actually has interesting mechanics to combine your spellcasting and warlock abilities.
I've always seen it interpreted that it only works for one side, but it's ambiguous enough that with a gullible DM you can probably get it to pass.