I haven't seen anything about how you plan to get rid of the debris. That's the most important part and most of the work. My experience is that in the long run the cheapest and easiest way is just to hire a dumpster. You want the trash off of your property, if you burn it or bury it there's always a residue that never goes away and turns up to pop your tires or cause other mischief.
After safety, the most important consideration is containing the mess. As others have noted, dropping the building takes a small fraction of the time of cleaning it up. The more pieces, the more cleanup. The ideal situation is to have the whole building broken into pieces that are just small enough to move with your tractor and fit in the dumpster. The nightmare scenario is a thousand pieces on the ground that you have to pick up by hand. The alternative nightmare scenario is a thousand pieces on the ground that you don't pick up and cause you grief for the rest of your life.
I would work backwards from where the dumpster has to go and how you're going to load it. Make sure you have a clear path for the tractor. When dropping the building, I would drop it onto something to contain the mess. If you're going to take the sheathing off you might want to lay it on the ground in the fall zone to catch debris. I'd even consider a tarp under the sheathing to catch nails and pieces of shingle.
