I have no tax advice, but wanted to chime in to say that an SUV offers essentially zero more utility than a van (I'm assuming you mean either a minivan such as a Dodge Caravan or a full size van such as a Ford E-250). A van will give you more cargo space, easier access to that cargo space, AND the ability to double as a large-capacity people mover. Even a minivan will be able to haul boatloads of 4x8 sheets of plywood/drywall, which most SUVs can't. And a minivan will get better fuel economy and have a more comfortable ride while doing so. Yes, you'll wear it out faster than if you weren't hauling freight, but you won't wear it out faster than you'd wear out any other vehicle.
Also, IMO, it seems like your standard of "beat to hell" is pretty fancy. I'm not sure where in the midwest you're located, but pulled up the Indiana craigslist page, and there was no shortage of trucks in the ~$5k range that I would absolutely put on my "call and possibly test drive" list. They're more than 10 years old, but this is a work truck, right? Or is it a fancypantsmobile? Anyway, a serviceable $2k truck with an $8k "if it breaks" fund sounds like a WAY better deal financially than a $30k new truck (that STILL may break...).