Wine (Is Not an Emulator)
Overview
As the self recursive acronym states, Wine is not an emulator. Is it a free software implementation of the windows API. It's purpose is to enable you to run windows applications on operating systems other than windows.
Performance
Wine's performance can be exceptionally good, close to windows in some aspects (even faster in a few test cases). It also supports 3D acceleration and looking into before other options for running windows software on linux. Adobe Photoshop and ZBrush 3.1 have both been confirmed to work in recent release of wine.
Ease of Use
Applications can be launched through the menu the same as with native linux applications and the software will appear in its own window, integrating well with your linux desktop environment.
You can get wacom support under wine putting a copy of wintab32.dll in your windows/system32 directory of your WINEPREFIX and setting wintab32 to native in your Wine DLL Overrides
Ease of Configuration
This varies substantially depending on the application being run. Ideally you will just run the installer with the command
wine /path/to/software/Setup.exe
If you're looking for a more user-friendly option than consider using Wine-Doors.
Though for a scalable production pipeline I'd recommend that you use separate $WINEPREFIX for each application you need to run and put this on the local harddrive of a workstation image. Because wine requires this directory and files within to be owned by the user running wine you'll need to make a custom temporary directory and a launch script. This should rsync the master directory for that application across to one for the current user within the custom temporary directory. Then change the ownership on that directory recursively to the current user and launch the application using that directory for the $WINEPREFIX. I realize this is quite involved, but it allows for the application to be made available to multiple users without requiring an installation for each one in their home directory, which saves on redundantly using space on your network drive, assuming you've made their home directory reside there.
Flexibility
The option is obviously limited to windows applications, it also currently only supports 32bit windows applications, but runs fine on 64bit linux.
Being able to install each application (or a set of applications) within a particular $WINEPREFIX allows you to have multiple applications which have mutually exclusive requirements running on the same machine.
Cost
Wine is free software release under the GPL and most likely comes with your distribution, or is available in its package manager. There is no cost in addition to the software you intend to run for this option, but if you need to use some libraries from windows (it is able to use these to assist in running some applications) you may require a license of windows, please consult a lawyer for advice on this.