I'm just going to be blunt. I don't think you will find a stroller that meets all of your criteria.
First of all a stroller that is going to do well on dirt paths and long walks around the neighborhood (1+ miles) is not going to weigh less than 20 pounds. And not only that, if you want one that is going to be good for shopping as well as dirt paths (ie not super wide wheel base), under $400 maybe be difficult as well especially if you want height adjustable handles.
If dirt paths and long neighborhood walks wasn't a requirement, I would recommend the Peg Perego P3. It meets your price, weight and adjustable handles requirement. You can take it for neighborhood walks but I had the very similar Zippy and I didn't really enjoy it for longer walks. It was fine for walking from store to store downtown but I really prefer the AT strollers for long walks. I definitely didn't like it for dirt paths.
The strollers like the Phil and Ted and the Bob Revolution are great but as you've noticed, they are heavier than you like. And I understand that. I have the Valco Trimode and one of the things that keeps it from being my one and only is the thought of putting it in and out of my car all the time.
And the few strollers that might meet all of your physical requirements, aren't going to meet your financial requirement. Although, I'm not even certain I can think of a single one that would meet those requirements. Oh, and I ignored the cup holder one because you can buy them after market.
Last edited by ellies mom; 02-23-2008 at 05:07 PM.
Miss Ellie 11/03
Baby Audrey 4/08