Maybe this can be a reality check, too, in a sense...but I have to ask what the proper amount of progress should be. When I started out, I had problems, granted, and had to work to get 2 miles in. Part of that as well is that I face a 3% grade when I go out of the house, and numerous hills all over the place. But very soon I got to the point of working up to about 10 miles with rests before I'd have to quit.
Now it's two months later. The good thing is that I'm to the point that I have to rest much less to go places (2 times on the last 10 mile ride on a fast stretch of ground I found - about 75% flat). The bad thing: My upper limit is still 10 miles.
So, is this generally expected for a 290# (yes little weight loss for riding 5-10 miles a day), or is there something that I'm not doing that I should be doing?