Halcyon, if you are going to change, I think Ubuntu 16.04.4 LTS is the best solution for a beginner right now. I think it is the most robust of the Linux varieties. I have tried the Ubuntu variations like Lubuntu, Xubuntu, Kubuntu, and at some point there has been issues that Ubuntu does not have. Mostly these issues can be resolved, but it is not easy for a beginner. Release 16.04.4 will last you till 2021.
If you are new to Linux, definitely try it out in Virtualbox on a Windows PC (make sure you turn on virtual PC support in the bios).
Wine can do some excellent emulations, but there is a lot of Windows stuff it cannot run properly - particularly programs that need drivers. Switching to Linux is a big trade-off. Mostly, if a developer writes a program for one platform only, it is usually Windows. On the flip side, Linux can do heaps of things easily that are very hard work in Windows - particularly if you do start to learn the command line. When I have to connect to a remote computer, I love it when I can connect to a Linux PC in a command line window. There is hardly a delay - everything happens instantly. When I have to connect to a Windows PC using RDP or VNC, I usually expect a frustrating time.
There are actually things you can do in Linux that seem like pure magic to a Windows user, and you also have the benefit in running an O/S that is a true server O/S. It does not have the built in limitations of Windows desktops like a maximum of 10 connected PCs, inability for running many server applications, license limitation of 1 person using a PC at one time and so on.
If you do switch to Linux, you will probably want to have a version of Windows running in a virtual machine just so you can run Windows-only tools if you have to.
When you have to upgrade from 16.04 to a new version, you will almost certainly have to reinstall. The GUI versions of Ubuntu do not tend to upgrade reliably and the chances of a beginner ending up with a blank screen, or things just not working fully are high. So expect that when it is time to upgrade, you will reinstall the new version of Linux.
Probably worth keeping a log book so you can record all the little quirky things you needed to do to get a package running perfectly.
Don't make the mistake in thinking that Linux does not need a decent PC. If you want a really good experience, start with something fairly powerful like an i5 or better, or a AMD Ryzen processor. 8G ram is minimum, but I would start at 16G.
You will not regret a SSD drive as the boot disk. All your work will end up in the /home directory, and at any time, you can move this directory to a bigger separate drive so a 256G SSD is fine to start with. If you plan to run Windows as a virtual machine, get a 512G SSD so you can also run the Windows VM from the SSD.
If I were transferring to Linux, I would probably run two PCs for a while. Just make sure you are using the Linux PC for email (like Thunderbird), web browsing and LibreOffice so that you can get used to relying on the new platform. Keep the Windows PC for a year or more so you can go back to it when you have to.