While it's doable, unfortunately running Windows software in WINE can be more of a hassle than a benefit. Therefore, it might be worthwhile to consider a locally installed virtualization solution such as VMWare or VirtualBox.
In either case, you'll be able to run "must have" legacy Windows software on your Linux installation, assuming your system resources have enough power to spare.
If possible, I suggest sticking with software applications that are native to the platform you're running. That means if you're needing to use more proprietary Windows applications than apps designed for both Linux and Windows, then switching operating systems could be a bad idea in some instances.
Getting your work done
As a general rule, most open source applications will give you the functionality needed even if the user interface isn't always as attractive as we might like it to be. Most challenges will be from end users thinking that the experience they had with the proprietary software will be similar to what they'll find with the open source alternative. For the most part, the end results will be similar, while the user interface and overall method of getting the work done will likely vary.
A classic example of this kind of software difference would, again, be with MS Office. The Microsoft ribbon interface was designed to make using their office suite easier. Unfortunately, if this is something you’re accustomed to, you will be in for a surprise when using LibreOffice.
Does this difference actually affect one's ability to accomplish a task? No, it doesn't do anything of the sort. But this difference may be enough of a hassle to create extra work for a new user.
Utilizing open source software to its fullest is best done by choosing applications that present users with only a minor learning curve. The less of a learning curve experienced, the better the switch to non-proprietary applications will feel to those affected.
Switching to open source the easy way
Making the leap to open source software usually starts with Firefox, as it's the gateway application for countless newcomers. And the best part is many people who have never used open source software before are likely already using this browser!
Once this is realized, the barrier to entry seems a whole lot less scary. The next step is to begin trying new open source applications that aren't designed to replace legacy software.
For example, if you needed a new FTP client, you could try Filezilla. This allows you to experience the application without the usual expectations of how it compares to proprietary alternatives.
It doesn't actually matter which open source software title you choose. What is important is that you try new software periodically as to break free from your comfort zone.
Once you make this a regular thing, the idea of trying replacements for legacy programs becomes a lot less invasive.