It's virtually impossible to screw yourself over in Pokemon. There is no random stat generation between levels, so the only reason you would ever worry about evolution is when considering what moves you want to learn. And with things like the move relearner, there is really no "optimal level" at which to evolve a pokemon. Also, TMs are now reusable, which makes it even easier to teach your pokemon good moves.
I do agree that the game does a poor job of teaching you these mechanics, but honestly anything works ingame. If you care enough about the more complex aspects of the game, you're probably using a guide anyway.