I've personally been on Linux since my Windows XP / Windows 7 days (used to dual-boot before gaming on Linux got hella easier). I learned that the secret to successfully sticking with Linux as a "daily driver" is to stay fully aware that it's not Windows, and trying to forcefully shoe-horn it into Windows-like habits is a recipe for reinstall.
First and most important Windows habit to break is downloading your software from random websites. Install everything from your Linux distro's "package manager" (basically similar to an "app store" on other operating systems, except it has nearly all of the software available for Linux in it). Only install software from outside the package manager when you've no other option available.
Secondly, you should not generally be trying to find ways to run your Windows software under Linux for the most part (unless there happens to be a Linux-native version available), but rather seek out alternatives to the software you'd normally use. Instead of seeking out programs by name or brand, seek out software by the task it performs. Look for the Linux program that does the task you need done (example; Instead of wasting time trying to figure out how to install PhotoShop on Linux to alter or create an image, try out GIMP or Krita).
The "easy-mode" way to find these software alternatives is this nifty website https://alternativeto.net/ - where you can search the name of a program you know does the task you need, and you'll get a list of similar software that does that task. You can then further filter the search results by software license, operating system, and other details. Also handy for finding neat software for your phone or tablet as well.
Anyhow, you absolutely should not be afraid to follow through on your thought to give Linux a try. It ain't nearly the same beast it was way back when I first started using it. It's generally for the most part easier to work with than Windows (and sometimes even easier than Mac), and it's lighter on system resources and runs on a wider range of hardware. You may find you enjoy it enough to install it on your entire network, as I have. Hell, I don't even keep a Windows virtual machine around anymore, thanks to WINE (and Valve/Steam's Proton fork of it) making even that need mostly obsolete for me.