I recently used Wine on Ubuntu and was amazed how smoothly it just worked. Download an msi Windows installer and open it just like you would in Windows. The program installs just like on Windows, and runs from its own icon just like in Windows. You hardly need to think about the fact that it's not Windows. Understandably there were a few compatibility problems but having it so well integrated into the UI was a surprise. It's perhaps almost good enough that you don't need to port your Windows application to Linux anymore. Just avoid the broken functionality. As a Windows programmer, I now keep Wine compatibility in mind when deciding to use new features and libraries and will be trying to remove incompatible code.
No real special sauce, but you have winetricks which has a few things to help solve common problems, and then winehq.org to see if others made a particular software/game on Linux.
I've found it to work remarkably well with games. Basically install Steam from Wine and then install Steam games like you normally would. It mostly just works.
I also installed and played "Path of Exile" through Wine with no problems. It's a fast, online hack 'n slash where if I died I would have to start over tens of hours of gameplay and Wine never let me down on latency or anything.
Wine does it everywhere. The way prefixes work it simlinks the traditional Windows file system heirarchy to Linux, such that XDG_DESKTOP_DIR or XDG_DOCUMENTS_DIR will become the Windows Desktop / My Documents folders.
It also generates .desktop files for Windows programs entries that populate your ~/.local/share/applications/wine/Programs folder and are thus indexed by most desktop application launchers. That means when I install Skyrim on Linux it shows up in krunner.
