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I've had this problem before. As best as I can remember it's something to do with the update failing to decompress files properly.
I think I got around it by using 'HackSteam' package. It's not as dubious as it sounds, it just causes the updater to decompress files differently.
To install it in PlayOnLinux, open POL and click 'Configure'. This should bring up a new window. In the left pane select the appropriate Wine bottle (the one with Steam in it). Then go to the 'Install Components' tab, select 'HackSteam' and click 'Install'.
This should solve pretty much all of your update failures. If you still get a failure just restart Steam and try again, they seem to happen randomly and you should be able to get past it eventually.
I've had issues in the past where my system updates borked POL's Wine versions (most recently with a pulseaudio incompatibility), but the System Wine still worked fine.
Usually with just plain wine you can install them with "winetricks"
However PlayOnLinux should take care of installing all those additional components for you. Unless you manually downloaded the steam installer from the steam website and told PoL to run it. Could that possibly be what you did?
If so you should delete it and add steam through PoL's list of available games, that way it knows exactly what additional components to install into that wine prefix for steam and it will download the steam installer and run it itself.
http://appdb.winehq.org/
Just search for the game in question and install whatever extra fixes are needed through POL's "install components" tab.
Wine version 1.7.23 with disabled dwrite from winecfg.
If those are already installed, try starting steam from terminal with -no-dwrite argument (wine /path/to/steam.exe -no-dwrite) to make sure that dwrite is disabled when you run steam with wine, because there is possibility that e.g. you have disabled dwrite to other wineprefix (?).
What is your wine version? (wine --version)