Totally Reliable Delivery Service

I got incredibly lucky and discovered something that made this plat possible solo and much less annoying. You DO NOT need to buy the DLC to use the powerups, there are two that allow you to just grab the package and fly direct to the drop off point, the helmet and the wings. In the starting city area there is a news building with a UFO beaming down near it, complete this challenge. You get a helmet that stops you from being knocked out/seeing stars from hitting the ground too hard. Next drive up the nearby mountain to the ski resort area, there is another challenge that gives you wings.
After completing that you can now crash into anything you want without the wings breaking as long as you have the helmet on. The only thing that makes you lose the wings is if you respawn after going underwater. It did make it look like I lost the helmet as well but I still had the effect of the helmet without seeing it on my head, if that is the case you can just respawn warp to the top of the mountain, start the wing challenge to get the wings and then cancel the challenge and your back in business. The only deliveries that gave me trouble were the ones with explosive items but I was still able to complete every one of them with the wings eventually.