Hey Nick, I wish you all the success on this. You're right it's kind of a Catch-22 between running better and weighing less. You might try a different aerobic exercise while you're building up your barefoot stamina again. I did a lot of rowing while I was working through my top-of-the-foot-pain, but now that my running is going well, I only row once or twice a week because it's so frickin' boring. Still, it's a good complement to running and weights.
As for diet, I have nothing really to add to all the great comments so far as well as your own accumulating knowledge, so I'll just write what I'm doing right now, in case it gives you some ideas. I've lost 30-35 pounds over the last 13 months, mostly through exercise, as my diet hasn't changed much--mostly I've just gotten rid of box cereal for breakfast.
Breakfast: mixed nuts and some dried fruit, one glass of OJ.
Brunch (I wake up around 4 or 5, so by 9am I'm hungry again): yoghurt with fruit (bananas, strawberries, blueberries, cantaloupe, blackberries). (BTW, I stir clear of all lowfat or nofat stuff. Right now I'm getting into the Greek yoghurt [I'm a little slow to hear about new trends].)
Lunch: raw veggies and fruit (carrot, cauliflower or broccoli, green apple, & grapes).
Dinner: grilled flesh and veggies (salad or grilled or cooked). Here I like to follow the 80% rule--never eat until you're completely full, so that when you wake up you're somewhat fasted, ready to eat. I usually have 1-2 glasses of beer or wine with dinner too. I should probably cut this out, but I'm middle-aged dammit, I need something to take the edge off!
I also read somewhere that you should eat your last meal 4-5 hours before you're sleep, so that your stomach is empty while you asleep (it's better at converting food to fat when you're resting). I used to do this when I was a bachelor, but with my present schedule it's not possible.
I've always been a pretty healthy eater, but now that I'm more religious about it, it's become downright hard to eat the occasion chip or pie. It doesn't taste good and feels like a rock in my stomach, so the better you eat, the easier it becomes, and your appetite changes. Also, now that my mileage is starting to increase, and my pace is up, my weight loss is starting to accelerate again. I know it's contrary to established opinion, but I feel like I burn more calories when I push my running, rather than doing more easy runs. I'm still about 15-20 pounds from where I would like to be, and as Ske says, the last bit to go is the gut--simply because that's the best place for your body to store fat, just as it's the best place to gestate a fetus.
Finally, I weigh in on the weigh-yourself-every-morning side. My weight fluctuates between 3-5 pounds first thing in the morning (well, second thing, after you know what), so I just record, on my running log, the new lowest weight when it appears. I just recently broke the 210 barrier, at 209, but today it was 210.2, and yesterday it was 213. Just normal daily fluctuations based on your daily food and water intake. I won't write anything down again until I see something south of 209, hopefully within a week or two.
All the best!