Hey bro,
Well....the thing I did for John Deere was a bit of a hack job. Basically I did this:
1) Setup a segmented plane as a cloth object.
2) Isolate a small number of vertices as affected by the cloth sim...set the rest as fixed (so just a small corner of the cloth starts blowing)
3) Run a sim for a for frames (maybe 0-20)
4) Re-edit the cloth parameters so more vertices are affected by the cloth sim
5) Run a sim for a few more frames (maybe 21-40)
6) Re-edit the cloth parameters so even more vertices are affected by the sin
7) Run a sim for a few more frames (41-60)
etc etc
The effect is that every 20 frames or so, a new "chunk" of the object begins to blow away (and this is caused by those new vertices being added to the cloth sim each chunk of time). Not sure if that will help you with your project, but that's how I did it for the John Deere one