re: umbrella strollers vs. joggers, etc.
I've never had a true umbrella stroller. With ds1, I had a fairly heavy duty stroller with a basket underneath, and a bag that hung off the handle and could double as a cover over his legs. It had three positions, from sitting straight up to lying down, and could be switched from front to rear facing. I loved it. I didn't drive when he was little, and that thing was wonderful. We covered a lot of ground together with it over 2 or 3 years.
With dd and ds2, we've used little strollers. We've had two of them, exactly the same. They're kind of like a larger umbrella stroller. They fold up pretty small, but have four wheels and a basket underneath them. They've also got a little hanging basket on the handle, which is good for snacks and a drink. They're not terrifically sturdy, but I find they have the convenience of an umbrella stroller (small and easily portable) together with the convenience of having some cargo space. More than once, I've gone grocery shopping and pushed dd in the stroller, and had ds2 in the Ergo. I've folded the stroller and put it in the bottom of the cart while we shopped, then let dd walk home, while I pushed the groceries in the stroller. It works out pretty well. The stroller cost us about $30, and we were on a very short budget at the time. (I really wanted one like I had with ds1, but there was NO way.)
I think the best stroller is whatever suits your particular lifestyle. DH and I have limited room, and a proper jogging stroller, as much as we'd have liked one in some ways, would be a huge storage problem.