P90X'ers and Fitness/Diet people... Need Input

Are you eating the calories you burned? Also, your maintenance level for calories might be a little higher than 2000. I would add 100 calories a per day a week until you start gaining weight/maintaining.

At that point is it best to grab those extra calories in the form of a Protein Shake/Bar?

Sure, especially if you are having trouble eating more. I would do it with just water for a week (Body Fortress Whey Protein from Walmart is cheap and tasty), and if you are still losing, add some milk for extra calories. It'll work best post workout, but any time is a good time for protein.

I'm at 206 lbs right now and I eat usually between 2500 and 3000 calories. It's not easy, but I usually burn in the neighborhood of 800 calories, sometimes over 1000 calories a day especially now because I do P90X and I'm training for a 10k in April. I pretty much eat all my calories back. That being said, some days it's just hard to make it. I try to pick calorie dense foods or include things that are calorie dense like olive oil. One thing I find that gets me every time, is that if I eat a normal but filling breakfast and lunch, normal snacks, and I'm not paying attention to how low in calories they were I find that by dinner I've still got 1500 calories to go! So, sometimes if I think about it I try to eat a large breakfast and lunch, that way I'm not trying so hard to make up the rest of the calories at night. Also, I eat another "snack" after dinner, usually close to bed. I know most people think you can't do that but calories can't tell time and your body still burns at night, and I work out at 5am before eating. It works for me I'm down from over 230 pounds doing that but opinions vary greatly on the eating before bed thing. For more info on that look up the hibernation diet, I get some of my ideas from it.

All that being said I am still losing weight, or at least inches and my fat percentage is dropping.

I have a great book called "Lean and Hard" by Mackie Shilstone. Mackie is a genuis when it comes to fitness and building muscle so fast on people you would think they were taking steroids. His "trick" really is to workout like a banshee and consume a crazy amount of calories. For a guy my size it could be anywhere between 4500 and 6000 calories. Look him up he's put muscle weight quickly on quite a few celebrities.

Also, try to eat more often, not just more at a time. Set your alarm to go off every two hours while you are awake. Every time the alarm goes off, eat or drink something (healthy). Try to eat a lot of healthy carbs in the morning.