Same answer as always: It depends on the game. A rogue-like with multiple save slots and save everywhere function wouldn't be much of a rogue-like, and a game like Celeste with permadeath would be absolutely no fun to the great majority of players. It all comes down to genre and gameplay.
What I can say about my preferences in general is that if you're expected to die often, the game should make sure you're able to jump right back into the action, without having to click through a lot of screens or menus, without having to re-watch long animations or cutscenes and without having to endure long loading times, because that also kills the momentum and motivation, not just the player character.
Oh, and I don't like it when death feels pointless, like you start again with full life at more or less the same spot you were killed without losing anything (by that I don't mean like in Celeste or VVVVVV, I mean games where you have actual health bars and lives but losing any of it doesn't actually have significant consequences). But I don't like too harsh punishments for death either, and tedious repetition is one of the worst for me. So bad checkpoint placement or the Dark Souls mechanic are kind of a no-no for me, too. I want to be mildly disappointed in myself that I didn't manage to stay alive, with a little setback maybe, but without getting really frustrated and bored.
And permadeath actually is one of the reasons why I'm not that much into rogue-likes, among others, but I don't think the games would be better with a save and reload feature, that would just make them more pointless probably. And I do enjoy the occasional rogue-lite, also because of the threat of failure.
The distinguishing criteria, I think, would be how much time your runs take (fast-paced and short is better in my book), how enjoyable the gameplay is, how much variation and how many surprises there are in retries and how much potential to learn something new. If failure just makes me repeat what I did before and the major part of it is not a challenge (or frustratingly challenging due to mechanics I don't enjoy), or if it takes ages to get back to where I was before, I hate it. If I don't lose much time over it and can jump right back into trying to deal with the very the thing that killed me again, or if it turns into a different, whole new experience, or I'm having so much fun with the gameplay mechanics that I don't care, it's fine.
Post edited February 22, 2021 by Leroux