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Yes and no for me
Distro doesn’t matter because they only differ in package manager and initial configuration, you can always compile things if you really need it.
GUI doesn’t matter because you’ll end up with all KDE and gnome dependencies installed anyway because your applications need it.
Experience probably matters, but if it doesn’t, it may be because there is just so much there to know.
Distro starts mattering a tad more once you starts experimenting with more esoteric stuff such as Guix, NixOS, QubesOS…