Man, I am dreading our next move (sort of). Ideally we won't need to move until we've managed to scrounge enough change out of the couch cushions for a downpayment, but you never know in this market when that will be.
Moving into this place (rental), we had sold most of our furniture items ahead of the move, but still managed to fill - not to the roof - a 26' U-Haul, my SportWagen (a couple of times) and my cousin's minivan once. I took the heaviest of the tools out of the tool boxes, and loaded separately. Not exactly space efficient, but it meant they were easier for two guys of moderate strength to handle. We had to move a bunch of stuff to storage in between places, so we amassed about 20 Rubbermaid totes for the lighter stuff, boxes for the rest. Heavier hand tools got distributed between tool bags, cordless power went into an old wood crate that I've had since I was a kid.
Since then, we have amassed all new furniture for the house including two queen beds, two couches, a three piece bedroom set, and dining set. The shop has grown vastly, adding a new 14" BS, 1.75HP TS, drill press, bench top planer and bench top jointer. I still plan to add a full-size 8" jointer to the shop, but that's likely the last big tool. The rest will be cabinetry and benches and materials.
In the shop alone, I can confidently fill a 26' box truck in no time flat. The house, easily another 26' I imagine when it comes time to move again. I'm less concerned, I think, about leaving the drawers full this time around, depending on the length of the move as far as the tool boxes, though the rest of the cabinets I'm not sure about yet. I suppose I have to finish building them before I determine if they're capable of moving full or not.