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One thing you could do is to enable a debug menu and 'Mark Errands as Complete' but that will disable achievements on that save file so that's not an ideal solution.
Wednesday, and I'm at the location talking to the old guy for the Breast Pump. Then I'm in the cow field and after walking around for about 30 minutes I realize it might be the glitch again. So i watched a walkthrough of Wednesday and realize I was never 'given' the bucket, and the old guy's voice never played telling me what to do. My last non-cow errand save was from Zack Ward, so I lost a lot of progress again. A common theme with this glitch is that these are the errands I am doing last.
This is some real ♥♥♥♥♥♥♥♥. I bought the DLC when it was brand new, and each time I tried to play it, something happened to prevent my progress. A year later and I try it now, and this happens.
I love Postal and RWS, but Jesus ♥♥♥♥♥♥♥ Christ, I'm never gonna finish this DLC.
I was able to reload the autosave from right before I killed the protesters and everything seemed fine. I just wanted to point it out that ~5 years later this was never patched.
That's about right for RWS. (I'm kidding, they're decent people)