It is more reliable to use a virtual machine or boot camp. It is more likely easier to use VM or BC as well. But, VM and BC require a copy of Windows.
Crossover Mac is based on Wine. Many Mac games, including games made by EA, use a wrapper based on Wine to port the games to Mac. Winebottler creates a wrapper for the software you want to use much like the game wrappers.
Compatibility is specific to each software you want use. The Wine website has a database that tells what software works and how reliable it is. The database also will tell you what dependencies from Windows you need to run the software.
Once you know what software you are going to use and what dependencies you need to run the software, using Winebottler is pretty straight forward. Winebottler provides a GUI to install and manage the commonly required dependencies.
Trial and error, in relation to dependencies, is sometimes required to get software with unknown compatibility to function. Some software will just not work. Winebottler does provide some feedback to guide you if you are able to understand the error messages it provides when you launch software that requires tweaking.
Wine and Winebottler are really more in the domain of geek tools if you are not using software that the Wine compatibility database gives a "platinum" or "gold" rating.
