I think the kid was trying to be conscientious, but when the splitter was dragging on the ramp, I could see how that stress would cause a crack.
He seemed to be doing the best he could with what he had. It's tough with our cars. There was a heavily modified S2000 that received some splitter damage being towed from a track day. It too was low and the splitter was big.
Sorry to hear about the damage.
- The damage seems to occur at about 3:18 . . . you can hear a big crack as the spoiler hits the deck followed by someone saying "Ooooh!" I wouldn't call the driver clueless: he had the right idea, but lacked the right pieces of wood to reduce the approach angle. The driver should have reduced the deck angle from the outset (as you or someone else suggested later) and he should have obtained appropriate blocking to get the car onto the deck safely.
The driver is presumed to be an expert in matters related to towing. Not having the right blocking is no excuse to keep going and damage your car. The bodywork should never have contacted the deck - allowing it to do so leads to a presumption of damage.
You're probably already engaged in the next steps. The tow company is required to identify their insurer - you file a claim with them. If that is unsatisfactory, I'd file a complaint with whoever regulates tow trucks in your area (usually a public utility commission), then file a claim with your insurer.
I once threatened to send a flat bed driver away without payment because he was about to damage my car. He stopped what he was doing and complied with my instructions (read from the vehicle's owner's manual) regarding winching, then completed the tow without damage to the vehicle. This video is a good reminder to all of us that YOU are always in charge when you obtain services for hire. If you see something that isn't going right, demand that the provider fix it or stop their activity. In your case, the blocking needed to extend up onto the deck several feet to account for the nose's big overhang. Maybe it's because I have experience building several sets of ramps for my Lotus to clear a high curb here at the condo, but it was apparent to me during the course of the video that the blocking placed by your driver wasn't going to work.
Sorry your car got damaged and good luck with a speedy repair.
Jesus Christ, why would anyone ever set the wood up like that? There's no way this guy has ever loaded a car with 2x4s because there is absolutely no reason to do it the way he did. Every single person who has EVER towed my lotus has put the ramp down on TOP of the wood to provide a more gradual slope.
I will add though, that as the owner of the car standing right there, you should be checking the clearance ready to yell "STOP" if it looks like it's going to hit.