First of all thank you to all of you who replied. I'm still trying to read them all :)

The problem I run into with this shot is that it's suppose to be an outdoor shot. Which could work with the spinning platform idea and green screen if done right. I'm making a war movie so it's suppose to be a shot of the main character and the villain fighting in the outdoors.

If there's other ways to do outdoor on a "grass" type terrain let me know. I'm going through all the posts still though so I might find it.

Grass is a strange terrain for roller blades... it just stops the wheels. ;)

As with most things.

Your only option for wheels would be something quite large, such as the diameter used on a bike, but I doubt that anything would be easy to work out for the shot.

Got access to a lawnmower? That would be amusing. Or, I guess, a dirtbike, if yo could somehow shoot from what while moving.

Your only real option here, especially as I'm guessing you don't have a way to suspend a device above the actors, even, is to have a cameraman with a steadying device and go for it.

Or greenscreen it, perhaps. Likely would look fake, without a lot of resources, though.

The only other options I can think of would be something that actually flies-- probably just a bit out of your budget; or you could design something that would have two legs, one on either side of the scene, then have the camera suspended from it, toward the actors, then each leg would be one wheels and rotate-- as you would need it to remain out of the scene.

Or, I guess, you could try to take out some device using FX, but that's probably not the best route, though might be needed.

Any idea where I can get one of the flextracks?

What about doing the shot in a place where there's a couple of trees and the trees can support in a way where you wouldn't notice some machine legs or something in the picture? Like have rope or something and then figure out how to get the thing to spin.

Well, whatever works. But I think you'd be better off just practicing running with the camera. For the same time (not to mention money) spent planning something else, I'm sure you could get it.

Yeah it would probably be easier on the budget :)

And if we get it steady enough perhaps it won't be too bad.

I now realize why I see this shot so much. It is literally the easiest shot you can do with a steadicam. You just zoom in a little bit, take a few steps back, and walk in a wide circle around your subject. Get a steadicam and you can do these all day