I've not been on this server since forever, but I found a WINE bug affecting me on TAKP.
If WINE has stopped working in the last few months you can try going to $HOME/.PlayOnLinux/wine/linux-x86/<wine-version>/lib and delete the 4 files with "libz.so" in the name.
I'd stick with a non-system version of WINE, since when your system upgrades it'll just put the updated, not-working, libz.so files back.
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