It’s perfectly fine to not be a stickler about rules, the real trick is finding a DM who is cool as shit and not all caught up with their own self importance as the controlling power of the game. Play to have fun and roll with it. As long as the group as a whole and the one player is still having fun, that’s all that matters.
“Camaraderie, adventure, and steel on steel. The stuff of legend! Right, Boo?” - Minsc the Great, uh, Philosopher Barbarian Ranger
It’s perfectly fine to not be a stickler about rules, the real trick is finding a DM who is cool as shit and not all caught up with their own self importance as the controlling power of the game. Play to have fun and roll with it. As long as the group as a whole and the one player is still having fun, that’s all that matters.