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And yes, you can fix the shirt-not-spawning problem via re-entering the map*. But with the quest not detecting your items, I think that resetting the map can fix that (but more probably I messed up). Also, maybe cheating the items in (IDs are 254/13) can help, but I'm not sure.
TL;DR: I'm on holiday, so I'll fix it later.
* I know I say it literally everywhere, but was your item spawn chance in Advanced config on 1?
It's not a bug, but yea it doesn't look good. (I can't fix it btw)
What sentences BTW? Like if they were rioters?
*22nd July probably
Or steal them from your careless comrades.