Here is my top four strollers for families. I picked these four specifically because of their versatility.

The Joovy Caboose:

This stroller has a regular front seat with a slide out bench in the back. It also has the ride on board if your big kid wants to stand in the back. The stroller can be used from 6 to 45 pounds. The canopy and basket are a good size.  (www.joovy.com)

The Bugaboo Donkey:

It can be used as a single with a basket on the side and it can also expand to accommodate a second seat (side by side). It includes a bassinet and a seat with a limit of up to 37.5 pounds. The basket and canopy are a good size. The stroller is expensive, with a base price of $1,295 for the mono configuration. (www.bugaboo.com)

The Baby Jogger City Select:

This stroller can be used as a single or double. This is the most versatile, with over 16 configuration to accommodate any child, from forward facing to facing mom to the kids face each other. The basket is huge. It has a weight limit of 45 pounds. In the single configuration the stroller retails at about $499. (www.babyjogger.com)

Britax B-Agile: This is the only permenent double stroller of the group. It has the biggest canopy and the air vent in the top of the seat, which makes for a unique feature. The basket is a standard size for a double stroller. The weight capacity is from birth up to 50 pounds. The retail price is $450. (www.britaxusa.com)

If you would like more in depth information on these strollers, please feel free to comment or email.