I got an iCandy Cherry with DS (now 3) and used it to walk a lot (most days 4+ miles) - and it's fine for this DC, so I would say worth the money.
Having had a cheaper umbella fold (as when he started nursery I could only leave a buggy if it could fold in one piece and the buggy store wasn't all that secure so I wanted something I wouldn't cry too much if it was stolen/damaged), I would say manoverability is very important once they get past the age of 1 and are heavy (and if you have hills near you!). Plus I hated him being forward facing (I missed our chats on our 45 minute walks into town, not knowing if he was ok, awake or asleep etc - you really do interact less with them when they are forward to rear facing, if you are only going to walk for a short time, not an issue).
Everyone said once I got the umbrella fold one that I wouldn't use the big buggy anymore, but I found if you've got a sensible practical buggy in the first place that's easy to push and rear facing, the slighter greater speed for folding/unfold and slightly lighter for lifting in and out of the car frame isn't that great.
Most places (I know John Lewis will) will bring a test frame out to your car and let you see if you can get it in the boot - those big wheels are a bad idea if you don't have a good sized boot, and check out the width of doors etc you might want to go through, the Cherry does fit though the barriers at the trainstation and most doorways, I know my friend bought the apple and that is slightly too big so she's aways got to open double doors of shops...
And really think about how you will use it, most friends have worked their way through 3 or 4 buggies by now (we all have 3 year olds!) - I'm usual in having just the original one and then an umbrella one I don't actually use much.
oh, and check out the after care of where you buy from, John Lewis if your buggy brakes will give you a "loan buggy" while yours is being fixed. I think some other big suppliers do the same, but if you get from elsewhere, worth having a sling or something in case your buggy is out of action for a week...