Another Starvation Mode Question

Is there anyone out there who was in starvation mode, increased their caloric intake, and was able to shed the weight?

I'm 25, 6' 250lbs, my BMI is 34. Last May I started playing tennis again, and play at least once a week. In January of this past year I added an hour of cardio and strength training twice a week to my program. I have eliminated soda, icecream, processed foods, and most recently red meat, and I haven't lost a pound in five months. I eat almost untirely unprocessed foods, whole grain/no trans-fat/nothing canned/little sugar/lots of fresh fruits and veggies/etc etc including drinking at least 8 glasses of water a day. I just can't figure it out. I've always been overweight (my 7 year low was 225lbs, high of
277), and I'm starting to wonder if maybe I'm eating all the right things, but maybe just not enough of the right things (or enough of anything)? I'm getting ready to add an additional day of strength and cardio (this is with a trainer and doesn't include when I go out and walk for 90 minutes - 2 hours by myself), but I'm getting very very discouraged.

I've had bloodwork in the past and everything is fine -- cholesterol, thyroid, sugar, triglicerides.

For several weeks. Typically between 1500 and 2000 a day (usually toward the low end). I don't eat a lot and I don't eat often, sometimes only once a day (I work full time and I'm a part time student). To give you some idea of good and bad:
6-8oz of orange juice large half-calf coffee with a splash of cream and two sugars (my one cup of coffee per day)
Blueberry muffin OR 1 cup of honey nut cheerios with milk and a bananna OR (very infrequently)
Bacon, egg, cheese bagle sandwich Turkey sandwich on whole grain bread and an apple OR Grilled chicken salad with honey mustard dressing Grilled chicken breast (4-6 oz), 1 corn on the cob, steamed green beans and broccoli OR (if I'm running around I don't have time)
Chicken grilled stuffed burrito from taco bell 1-2 sticks of Extra Gum (1 calorie)
4-6 Altoids A few handfuls of peanuts (lightly salted, not honey roasted) OR A couple slices of whole grain bread with natural peanut butter on them (3-4 tbsp at most)
OR Carrots, celry, and dip OR Fresh strawberries and pineapple cut up Water all day A soda *maybe* once a week (but more likely a lemonade)
8-12oz of Gatorade 2-3 times a week (usually the days I run or play tennis)

I can tell you I never have a "bagel sandwich breakfast + grilled chicken lunch + taco bell dinner + 3 of my snacks in the misc column".
My trainer is a nutritionist, and we removed most of the hidden sugars and processed foods from my eating months ago. When I eat out I've cut all my portions down to 2/3 or 1/2 of what I used to eat.

Not to be a whiner, but I have cut out a tremendous amount, anything more reaches a point that isn't sustainable (I don't do fad diets). My
"diet" is my way of eating, it's not something I do for a month. I knew I was at a breaking point a couple weeks ago when I gave up beef (again though, I only eat lean cuts and my portions are never more than 8 oz), and still nothing.

I have counted calories. I probably should have mentioned that I have been on just about every diet known to man: the only time I was "thin" was in highschool when I ran 5 days a week and ate six times a day.

Which, honestly, was my original goal when I started making changes last year. The discouraging part is that I eat healthy and I exercise,
I just can't seem to shed a pound.

Which I think brings me back to my original question. If my AMR/BMR says I should be eating 2300-2500 calories a day, and I'm consistently eating 1500-2000 a day, why am I not losing any weight? Has anyone found themselves in starvation mode, and changed their eating (maybe not even increased calories, but made sure they ate 4-6 smaller meals instead of 2-3 larger ones) and found that made a difference?

In a few weeks, I'll have some more time to raise my activity level, but that will only last for about 8 weeks until the fall semester starts again, so while I'm willing to do more exercise I won't be able to sustain an increased level -- I need my metabolism to meet me in the middle. I know for a while that I was converting fat to lean muscle (and I've noticed a huge difference in my arms and legs) but this plateau is getting old, I might as well go back to a steady diet of Ben & Jerrys washed down with some Oreos. At least then I'd enjoy every single bite.