Scenario: You're playing an 18th level character you've run since first level for over 3 years in real time. He's the leader of the party, and the hope of middle-earth. He's defeated dragons and hordes of undead. His magic weapons are legendary. This character is really part of YOU. You've played with him every week for THREE years.
Your party is on their way to the island fortress of the Demon King for the final epic battle. It's gonna be awesome. The entire campaign has led up to this. You have to swim across a river to reach the castle. You roll a 1 on your swim check. You get another chance, and roll a 2. One more chance, roll another 1. You are swept away and drown. Your character is dead. You miss the final epic battle, because you had a bad stroke of luck, and the greatest hero the world has ever seen drowned in rather unheroic fashion.
You're totally fine with that?
I'd like to think I'd be smarter than to put my treasured 18th level character in
any danger of drowning so unheroically (I can't take 10 on my Swim check? I don't have Boots of Water Walking? Wings of Flying? A frickin' Potion of Water Breathing? Ooooookaaaaaay...) but let's assume I find myself in a situation where the rules essentially boil down to: if I roll 1, 2, 1, in that order, my character dies.
Well, then
that's the game. I've weighed the risks and made my choices, and now it's time to experience the consequences. Otherwise,
why am I rolling dice in the first place? If I really don't want to have any chance of drowning, there's no need for a die roll, I can just announce that my character swims across the river and emerges safely on the other side. To me that sounds like less of a game and more just telling a story, but if you think the
game should be all about killing bad guys and not swimming across rivers, then go ahead and save the dice-rolling for the bad guys and gloss over the river-crossing.
So to answer your question...
yes, I'm totally fine with that. It is, at the end of the day, why I haven't gotten bored with D&D after playing it for over 30 years. Because I never know, when I make a new character, whether he has some great, heroic destiny in his future, or will turn out to be just another would-be hero who didn't quite make it (or never even came close). And sometimes, the stories about the ones who failed are more memorable than the ones who succeeded.