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Jarrett2, I actually totally agree with what you just said, and I don't think that what you've said and what I said are really out of whack.
My own personal goals include both becoming a stronger cyclist and also losing weight. I'm no racer, and never will be, and as a fat body I don't have the luxury of eating a ton to fuel long, hard training rides like a thinner cyclist can do. That's why I'm pushing myself to train my body for better fat adaptation, so I can ride long and hard while also losing more weight.
I totally agree that someone just trying to lose weight will do far better by focusing entirely on diet, and then using some cycling as a boost to burn a few extra calories and get the metabolism working harder. It's fairly easy to cut 400 or 500 calories from the diet, and to burn those same calories a guy might have to ride 15 or 20 miles. Eat 400 or 500 calories and then riding 20 miles nets you really nothing except some cardiovascular endurance benefits and some improved muscles that may pay off in terms of improving one's metabolism. Getting to where one can both cut the 500 calories from the diet and also ride 30 or 40 miles without eating those calories back is the bonus round. Really good weight loss, and also some legit cycling improvement.
I think with a month on the trainer and 50 miles on the road it's a pretty good time for dfull to decide what his goals are, as you suggested. If he's liking cycling and wants to do it long-term, not just for weight loss but because he enjoys it, as I do, then I think it's smart for him to plan out how he's going to build up his cycling endurance, while also losing weight, and this is where energy management comes in. If he's only riding 10 miles at a time I doubt there's any reason to eat anything at all for his rides, especially since he'll never burn it off in just 10 miles. Of course he apparently bonked in 9 miles in a good headwind, so there's that. He probably wouldn't have if he had a better developed cardiovascular endurance, which will come with setting some distance/heart rate goals for building a good base, and sticking with it.
If I go on a fast group ride I'll take calories in before, and during a ride, and then make sure I eat some protein and a small amount of carbs immediately after the ride. I don't consider group rides to be "weight loss" rides, so if I blow half or more of the total calorie burn of the ride by food/energy intake, I'm OK with that. My weight loss rides are my solo rides, where I can ride at the pace I think will most benefit me in terms of burning fat and training my body to become more efficient at burning fat. My ultimate goal is to become so well fat adapted in my cycling that I can do these same 45-50 mile tempo group rides without taking in any external calories. I'm just not there yet.