The numbers...

On "My Account Home"  it says my Daily Goal is 2300 cal.  When I take the quizzes to find out how many calories I should be eating to loose by my goal date, it says I need 1356 a day.  Where does 2300 come into the mix? 
I have been averaging about 1244 calories a day for the past week since I signed up, and I walk/run on the treadmill, burning between 250-300 calories 5 times a week.  I also do 20 minutes of Pilates (80 cal) 5 times a week.  Is this enough?  
BTW, I'm 5'7" and 155.  I'd like to get to 150 by Thanksgiving.

What did you enter for your activity level? I believe the daily calorie goal is tied to how active you are. I think your cardio is ok - although you should be doing intervals for weight/fat loss rather that just walking and running at a steady pace. If you run for a minute, then walk a minute to recover, that's ok - but run as hard as you can for that minute. As for Pilates... I teach it, but it's not a good muscle builder or calorie burner. You'd be much further ahead if you dump the Pilates and lift weights. Pilates is ok for strengthening your core, but that's about it. Hit the weights, do interval cardio, and you should be close to your goal by Thanksgiving.

I entered "light activity" in my account settings and I'm not sure if that's right.  I'm a instrumental music teacher so I pretty much sit around teaching lessons all day.  But at home I rarely sit down and watch tv.  I'm always busy doing something around the house.  I do cardio and pilates 5 days a week.  Do you think this is the right "activity level" for me?
As for the treadmill, I have been doing intervals.  Right now I have been doing this pre-programed workout on my treadmill that has me walking at a good pace, then running fast a minute, moderate a minute, then jogging, then walking again, then up a steep hill, then less of a hill, and less, then walking again.  This pattern rotates for 40 minutes.  I feel really good after.  Is this a good workout?
Same with Pilates- I feel great afterward, and my core is solid!  I love it!  Thanks for the advice about the weights.  I will add that in.  Should I do a day or two less cardio and replace those days with weights?

The 2300 amount you see is probably the default Base Metabolic Rate calculated when you did the initial questionnaire.

You can set your "goal" calories at the bottom of "My Account" -> Account Settings.

What does the blue box on "My Account" -> Home say for total estimate (under burn meter)? I'm guessing its also 2300.

I'm not an expert, but from what I've read here, you don't want to have a deficit of more than 1000 cal/day. If your BMR is 2300 and you're also doing 300 cals of exercise a day, you'd want to eat at least 1600 cals a day.

Also, it takes about 3500 cals deficit to loose 1 pound. 5 pounds in 2 weeks is probably about the most what most people would consider a healthy amount to loose (1 or 2 pounds a week is what seems to be the consensus). So a 1k deficit a day would put you pretty close to your goal.

Good luck!