You shouldn't be so hard on yourself, as you have made very good progress thus far. I believe the key to health is balance. If one is too strict, they are bound to fall back into the wagon, or however the devil that saying goes. If one is too lenient, they are making no change and will, therefore, see no results.
My advice would be: Do not worry over the scale. A person's weight tends to fluctuate, so it is best to check once every two weeks at about the same time.
Good luck in your endeavors.