Games

I thought the same, especially since I had tried Linux on my main several times since the 90s (my first dual boot was with Slackware).

Then maybe 8 months ago I did the transition, and installed Pop!OS since I'm a gamer plus I have a NVidia graphics card and didn't want to go through the whole hassle related to that (Pop!OS has a version which already comes with those drivers).

Mind you, I did got a separate SSD for Linux and meanwhile added a new one, which is where my games directory is mounted and upgraded the root one to something a bit bigger,

So, this time around, what did I find out in about 8 months of use:

• Once, I did had to boot into CLI mode and have apt do some failed upgrades, which included doing some kind of rebuild thing (you get instructions of what command to run when apt fails). This was due to a upgrade of the apt itself, I believe. All the other times it just boots to graphics mode (I'm using X rather than Wayland) or if it fails to start it (happened only a handful of time) you just reboot it.
• In general even though I've done things like add and change hardware components, I have done little tweaking via CLI and some of it I did it because I'm just more comfortable with it or wanted so obscure options (for example, I wanted to mount the drive shared with Windows with a specific user and group, so I had to edit fstab). Except for the more obscure stuff there are UI tools for all management tasks and one doesn't have to actually do much management and things almost always just work (for example, I changed graphics card - whilst staying with NVidia - and it just booted and worked, no tweaks necessary)
• As for games, I use Steam for Steam Games and Lutris for all other game versions including GOG. Both have install scripts specific for each game, that configure Wine appropriately, so you seldom have to do anything but install, launch and play. That said in average I have had to tweak maybe 1 in 10 games. Further, about 1 in 20 I couldn't get them to work. If you do install pirated games, then there is no install script and you do have to do yourself the whole process of figuring out which DLLs are missing and configure them in Wine using Winetricks (curiously, I ended up having to install a pirated game because the Steam version did not at all work, and the pirated version works fine). Note, however, that since I don't do multiplayer games anymore, I haven't had problems with kernel-level anti-cheat not working with Linux.
• Interestingly, for gaming you have safety possibilities in Linux which you don't in Windows: all my games launched via Lutris are wrapped in a firejail sandbox with a number of enhanced security restrictions and networking limited to only localhost, so there is no "phone home" for the games running via that launcher (Steam, on the other hand, is a different situation).

I still have the old Windows install in that machine, but I haven't booted into it for many months now.

Compared to the old days (even as recently as a decade ago), nowadays there is way less need for tweaking in Linux in general and for gaming, even Windows games generally just install and run as long as you use some kind launcher which has game-specific install scripts (such as Steam and Lutries), but if you go out of the mainstream (obscure old games, pirated stuff) then you have to learn all about tweaking Wine to run the games.

If you have a desktop and the space to install the hardware, just get a 256GB SSD (which are pretty cheap) and install a gaming-oriented Linux distro (such as Pop!OS or Bazzite) there, separate from Windows and you can dual boot them using your BIOS as boot manager: since the advent of EFI, booting doesn't go through a boot sector shared by multiple OSs anymore, so if you install each in their own drive then they don't even see each other (you can still explicitly mount the Windows partitions in Linux from the Files app to access them, but otherwise they have no impact whatsever on booting and running Linux) and only the BIOS is aware of the multiple bootable OSs and you can get it to pop up a menu on boot (generally by pressing F8) to change which one you want to boot.

For the 20 or 30 bucks of a 256GB SSD it's worth the try and if you're comfortable with it you can later do as I did and add another bigger one just for the directory with you games (or your home directory, though granted to migrate your home like this you do have to use the CLI ;))