Installed Steam with the standard package, after the first update
Steam quit and got stuck on "Updating Steam..." every time I tried
to start it. Then I downloaded the MSI package from the Steam
website, installed in a new bottle and the same thing happens (but
without needing to update first).
The 'cancel' button doesn't appear to work and I need to quit the
bottle to reset it.
The system log contains this:
2/2/12 4:42:39.547 PM warmd: [_bootcachectl_save_playlist:1236]
Assertion failed: (error == 0): Unable to save playlist to
/var/db/BootCaches/C15C1786-3DDC-4BCA-99CB-DC76B8CA25FE/app.com.codeweavers.CrossOverGamesHelper.Steam-2.Steam/.Steam.playlist:
2 No such file or directory
I can't speak for WineSkin and only because I haven't tested there recently.
Steam does install in CrossOver and Wine without much trouble.
When you installed it a second time via CrossOver, did you specify the path to the MSI installer? CrossOver will continue using the first version it downloaded unless you point it at the new version. The error message you are receiving is a bit strange and I fear there may be something else afoot with your system. You would likely do better to send in a Support Ticket (or email info@codeweavers.com).
You will likely be asked for the specific version of the MacOS you are using, the specific version of CrossOver and you may be asked for the log file from the attempted install via CrossOver. The final bit that may be interesting is your clean Console log from the attempt.
The reason I believe this may be more specific to your system is that if it was occurring for everyone we'd have many, many more reports (and we'd be able to reproduce this in-house). Because that is not the case, we'll need to do additional debugging with you to help you.