Alrighty... A few things about the latest release of wine (the one thats now found in the ubuntu PPAs)...

Since wine released version 1.5 everything - and I mean everything just seems to magically work bar a few really specific programs which are quite new to the scene. The WineHQ appdb as such tends to have a lot of outdated tests. Also it now supports 64 bit windows programs which can make setting up stuff a tad harder, but just google up something with the terms 'wine1.5' and the number of bits you want and how to setup basic dependencies you think you might need.

As for testing - the best way is to make a new and separate wine prefix so that if you end up accidentally nuking something or messing something up all your apps still work fine. Thats actually easier done than said:
Code:
mkdir .thenewprefix 
#makes a hidden folder called thenewprefix which will be our wine prefix
$WINEPREFIX=/home/$USER/.thenewprefix wine setup.exe 
#runs setup.exe in wine using the new prefix
note that you might want to do a winecfg in your new prefix just to set up some basic stuff before delving straight into that. Though some compilers can cause some weird behaviour and crashes under wine, the last time I did this was a few years back and lets just say wine had some trouble with the most basic of apps and really doesnt reflect the current versions. Personally, I think wine 1.5 is well worth the hassle since the ironic realization that more windows programs work under wine on linux than work on windows 8 sort of speaks for itself