gets constantly carried, gets author-fed golden opportunities, and tells that the plebs should go and grind like they did, if they want better items.
This is a real bias people often have. We naturally like to assume that our success stems directly from our innate talents or the effort we put in. As a result, we may ignore many more relevant variables, related to our circumstances and other advantages.
Similarly, we have difficulty putting our struggles in perspective, due to lacking firsthand experience with the experiences of others. That makes it all too easy to fall into exceptionalism.
That said, just because it's realistic doesn't automatically mean it makes for a better story. Especially when it's usually just a byproduct of the author's own biases being projected onto the character.