I have been using a Joovy Caboose($170 at Amazon) almost daily for two years now, so I'm pretty qualified to review it. This is not a freebie review -- I'm just sharing my experience for some other moms who have asked:
First, I love being able to say I'm "putting my kids in the Joovy" to push them around town. Hilarious name. The thing drives me crazy pretty much daily, and yet I don't really think any comparable product on the market would be better.
The things that drive me crazy are that it's a little hard to turn and push (partly because my axles are pretty rusty, though -- if you don't leave it out in the rain as much as I have that won't be so bad) and it's heavy to lift. It's hard to hang a purse or a bag on the handle, and since the basket is so small that's annoying. It also has no cupholder which annoys the crap out of me. You can buy one to hang on there but I have not done that.
Also, the front seat is pretty small and so now that my baby is 2, even tho she's small for her age, her feet hang past the footrest. Soon, of course, I'll have my new infant in a carseat in front and the toddler in back and the then-5-yr-old will just have to hoof it or she'll be at school.
It is not an all-terrain stroller and doesn't handle bumps or snow particularly well. In fact, if the little one is riding in the back seat not strapped in, going over a big bump has sent her flying right out of her seat.
I have pushed it through a lot of snow on sidewalks (with mighty effort), but when we get to the pile at the corner we're in trouble. I'll make the kids get out and lift it but that's not great either.
It has a lot of good points, though. The whole sit and stand concept works like a dream -- both my 4-yr-old and 2-yr-old love being able to hop on and off the back seat. They fight over the back seat now. Also if you have a couple bigger kids with you, they can both stand up on the step together and you can push them all. I can get a surprising amount of groceries on this stroller by hanging bags off the side handle things, and since the frame is metal it easily takes all that weight.
I feel quite comfortable in stores with it, since it is about as compact as you are going to get for something that holds 2 kids -- nice and narrow and not terribly long either. It fits fine in the checkout aisle of the grocery store.
My dad pushes it a lot when he takes my kids to ice skating, and he dislikes it so much he wants to get me a fancy new double stroller for a new baby present. I'd take a jogger that handles snow better, but I'm sure he'd pass out if he saw what those cost.