I think almeeker pinpointed the downside to the gym&calorie consumption plan. A good general rule is to eat 9-13 cals per pound, depending upon the weight loss you want to achieve and at what rate. 9, in my opinion, is pretty drastic (I love food!). A safe bet would be between 10-11 per pound. This method also takes into consideration weight shifts. Then, all the work you do at the gym would just be gravy.
Also, since you're using fitday to log all your calories, try to look at it from a week's average perspective. That way you don't have to beat yourself up if you've had a bad day or have a "cheat day". All because what it comes down to is calories in and calories out. By taking it a week at a time, you lessen the stress and the OCD over daily caloric intakes.