I daily drive Linux mint and love using fish, I do have a custom built NAS but I rarely ssh into it, so I’m not limited by it, but as some mention that if you’re a dev and do a lot of SSH/remote controlling then it might work against you if you form too many habits.
The simplest and the most windows like in looks distro would be Linux mint, it’s probably better than trying Ubuntu or other distros for your first experience with Linux.
If you want a challenge then go for it but just letting you know it’s better start off with a few wins under your belt then getting freaked out by complex systems like fedora made for advanced users.