We own three strollers, and I have to say I use all of them from time to time. I love to wear my DD2, but sometimes the stroller comes in handy for her or for DD1 when she gets tired.
When DD1 was born, we bought a big honking travel system by Evenflo, and the stroller is still used a LOT. DD1 used the infant carseat (DD2 didn't) and it snapped right into the stroller, making it possible for her to face me when we walked, and to recline and nap comfortably. We bolstered the inside of it with some rolled up blankets to make it more comfy when she was a little baby. Our choice of this travel system was almost completely due to two things -- there are TWO CUP HOLDERS in the top, and there is a HUGE HUGE HUGE basket underneath. Many was the time with DD1 as a baby where she was in the sling but the stroller basket and the stroller seat itself held coats, diaper bag, mall purchases, groceries, etc. The stroller looks beat-up after 4+ years of use, but it still works just great. We call it The Tank.
The second stroller we bought was a GREAT purchase. It is a couple-year-old version of
this Chicco umbrella stroller...and it's wonderful. It lives in our trunk and is used for things like the Botanic Garden, going downtown on the train, shlepping into huge superstores like Ikea, etc. It is also WONDERFUL for travelling in airports and out of town -- lightweight but strong, comes with its own carry-bag, has little pockets for things like cell phone, keys, snacks, etc., and has a little basket underneath that will hold (and this I can tell you from experience) a maya wrap, a child's jacket, a bottle of water, and a couple of small toys. This was the best $50 I spent as far as travel gear. A GREAT stroller.
The third stroller I bought is a double stroller -- not something you'll need -- but for anyone who's wondering, if you buy a cheap double stroller, you get a cheap double stroller. I hate using it and don't unless I have to...I'd rather sling the baby and push a single stroller if DD1 wants to ride.
Good luck! I think you should go to a store and try out a bunch to see what you like. I never saw a $700 stroller that I thought was worth it, but my friend SWEARS by her Bugaboo...