PlayOnLinux is more like CrossOver in that it can set up specific wine directories per application with app-specific overrides. So if wine 1.5.22 breaks MS Office 2010, PlayOnLinux can set it up to that MS Office 2010, and only MS Office 2010, has a wine setup that is actually 1.5.21.
Its more than just "a frontend."
To manage prefixes you can use $WINEPREFIX, if you write some scripts you get it too*.
The part of manage wine versions is just not a part of wine's job.
Wine never works out of the box with most things, but neither does Windows. In fact; allmost all classic games need patches/cracks to work on anything that's older than Vista. There's a reason Windows software employs DLL versioning, and almost any Windows app ships with the DLL versions that they were developped against.
Ofcource, if you keep buying/installing anything that requires the latest Windows release, Wine will keep being behind on support, for obvious reasons. That is where virtual machines are for.
But for me, Wine is like Dosbox; it keeps legacy stuff running, and Windows simply doesn't.
Wine usually has been working quit nice for many years, and for many things.
However, what really bugs me is when in order to get your fav game working you need that one-liner fix (literally!), and for that you need to recompile the whole shebang. In a 32bit chroot. With hundreds of -dev packages. And nightmares.
And when there's a new version, the patch isn't intergrated, but just needs to be applied to a different line number. And you have to do it all again. sigh
My Gentoo install makes compiling and installing so easy .