I sort of like your idea. I enjoy the creativity around here.
I do think it should have some serious experimenting before hard-charging forward into, but I think it has some promise not only for windmills, but for other low-cost pop-up, portable tower models.
From what I think I follow of your application, you are talking about using dead-weight barrels in lieu of anchors for guys? Those are the four barrels in the first paragraph? Am I understanding that correctly?
If that is the case, a caution I would add it that for guy wires, side wind loads are not JUST pulling upwards against a dead weight. There is a sidewards component of the force the guy cable creates. In the model I think you are describing, one would rely on the friction across the ground surface to resist those sideways/horizontal components of the force. Does that make sense? If not, I can draw a picture? Anyway, those friction factors will vary greatly depending on what surface the dead weight barrel is placed on, and even temperature. That could make the modeling math get pretty wide ranging.
I guess a "test" could be to put an equivalent tower rig up and hook it to the back of the truck and give it a "pull it over" test that is at least a couple times the greatest windload.
I was pondering using a free-standing (no guys) tower with a water weight base here >>> http://www.fieldlines.com/story/2005/10/2/172335/302
But mine was more "thought experiment" rather than getting ready to build. Dunno if that will give you any helpful ideas or not.