Application support under Wine can be hit-and-miss. 
Your OS X-based data can be accessed from your Window programs. You don't need to buy a copy of Windows. Some commercial software is delivered for OS X this way - I know The Sims 3 game that my wife likes to play on her MacBook Pro is actually the Windows version of the game running under the Wine emulator. The free WineBottler and the paid-for CrossOver Mac from CodeWeavers. It sits between the Windows application and OS X and makes the application think it's running on Windows by translating all the Windows calls its making to OS X calls. It's a bit like a virtual machine but doesn't require the Windows OS. 
Wine is a translation layer for Windows applications.
If your Mac is older, doesn't have much RAM, the VM approach can drag down your system a bit but most, if not all, new Macs can handle VM hosting duties without much of any issue. 
The Windows OS installation will take up a lot of space on your hard drive, plus the Windows application space.You have to buy a copy of the Windows operating system.You get a bunch of neat things with virtual machines including the ability to pause applications mid-run and snapshot the state of your virtual machine.Decent support in the commercial offerings at least for graphics acceleration so you can run some graphics intensive programs.Can pick between running them in a full Windows desktop-in-a-Window or in integrated mode where the Window apps appear as windowed apps right in your OS X desktop.
Your OS X-based data can be accessed from your Windows programs. Near native speeds for your applications. And if you're comfortable tweaking and fiddling you can use VirtualBox for free. You have VMWare Fusion and Parallels Desktop in the commercial space to chose from when it comes to virtualization software. They all come with pros and cons Run a Virtual Machine
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