Even if the stories don’t connect, I always would recommend starting at the earliest point in a series and moving forward, since this allows for a better appreciation of the evolution of the game over several iterations rather than being disappointed by the regression you would see going backwards or jumping around.

How do you approach remakes/remasters, franchise reboots, and prequels in that case? Do you play them in release order?

I think taking that approach would put a lot of people in the situation where they are forcing themselves to play something they don’t really want to. How many people have gone back and played TES Arena or even Morrowind?

Maybe it’s because I like completing games that I start but I feel like just trying every game that lead up to Skyrim would get tiring in a hurry.