I don't own a Kennedy, but I've seen quite a few of them. The older tool list at the school I attend had a basic three-drawer Kennedy top box on it... a few guys now have an 11-drawer. And even they say they aren't that good of a box! Well, it's true. No ball bearings, which is something I love. I don't think any toolbox is worth $300 for a small top, or $500 for a large one, though...
My toolbox setup at school is, on top, a basic Waterloo three-drawer which is fine, but it has no ball-bearings, so to me it may as well be on par with a Kennedy. Fit and finish isn't as good, but I really don't care about that. Guess what - for a bit less fit and finish, I saved a bit over 200 bucks over a three-drawer Kennedy...
Middle is a Kodiak three-drawer I got off of Amazon because it was cheap - $75 or so. Though it was shipped dented, I was able to fix it, and it has ball-bearing drawers.
The bottom is a WorkSmart five-drawer, which I absolutely love. Nice fitting, ball bearing drawers which close easily. Only thing I don't like is that they come open if I move the box, but I can lock it to fix that. A Kennedy of the same size, without ball bearing drawers which are most important in the bottom, where heavier items should be kept, would be... heck, I don't even know. The WorkSmart was $285 from MSC.
So... I think, if I were to buy an entire toolbox setup, I'd probably go with WorkSmart. The tops I've seen have ball-bearing drawers, and the bottom I have is fantastic. Some guys like Kennedy, that's great, they do look nice... but, I just love them ball bearings!