Start with Linux Mint. It should be a very pleasant and straightforward experience right out of the box, and is just in general very beginner friendly. I recommend to create a live USB (basically, download the ISO from the Mint website, then use something like Balena Etcher to put it on a USB stick). You can then boot off that stick, and try Mint out to your heart’s content, without risking your Windows install or data at all.
Can I ask, what are the programs you wager you’ll have to emulate through wine?