He is built very long in the torso, and is very comfy in the Vogue; it is his favorite buggy of all. (I own a total of 5 strollers, among them a Chicco Fly2, which the previous poster asked me about. You might say strollers are my hobby,

) His head still clears the Vogue's hood by at least 3 inches. He is technically over the 40 lb. weight limit, but it still steers beautifully.
The best thing about Maclarens is their maneuverability. Even with a heavy load, they still steer like a dream and roll without effort, much better than any other non-jogger stroller on the market. Personally, I prefer to use a bag slung over the handles while at WDW, we don't use the basket much. With a bag, I can just grab it off to go into rides or get on the bus.
Baskets are more trouble, IMO, and I've found that travelling lighter is very liberating. I use a neoprene bottle sleeve with a belt clip as a cupholder on my Maclaren, it works just fine, and you don't have to remove it the drink when you fold the stroller.
If you really want a compact stroller that will last through heavy weight, your best bet is a Peg Pliko. Those are rated for a total load of about 90 lbs. They are a bit heavy for an umbrella fold design, though, about 14 lbs, as opposed to 9 for the Vogue. The new 2002 models have added compact cupholders for parent and child.