Re: You wouldn't have stop the caravan.
You can't shoot at your own convoys from a helicopter. Not only are the chances of terrible accidents far too great (air to ground fire is hideously inaccurate, that's why we give aircraft such big guns :).
Plus, you never want to create a situation where a handful of enemy soldiers/troops/zealots can result in your own convoy being shot up by your own (asset). Situations like that historically become tests of bravery, criminal sentences and civilian extortion tactics (run out there and make them shoot at you or your child/wife/mother gets it). The negative press alone would be a nightmare.
The poster above is correct, convoys without ground support were already proven to be a nightmare in the past. That's why we send so many troops on supply/logistics missions today.
Honestly, this seems like another expensive complication to a very simple situation. If you take a look at most post WWII Western military strategies and tactics, you can plainly see the rise in technology and 'designer' tactics dreamt up in a classroom and how it rises in direct proportion to the cost of the campaigns and how fewer and fewer of the initial campaign goals are met.
The technological commercialization of warfare,and the introduction of complex, 'process based' academic strategies that require things to happen in a very specific order has been fairly disastrous. The entire concept of a 'thinking mans' war has always been epically stupid. Behavioral science falls down instantly and completely when you blow up someone's house with their family inside: All bets are off.
For thousands and thousands of years, the first thing soldiers destined for leadership were taught was that plans, superior weaponry and expectations are nothing more than peacetime tools to remind soldiers what their job really was. None of that stuff mattered, at all, once the first rock, spear, arrow, cannonball, bullet, rocket or missile was fired.
A modern US soldier, who signs up for a 2nd enlistment, has had more than $1m spent on his equipment and training him to use it. They still die in droves fighting goat herders using weapons made in countries that don't even exist anymore and explosives a chemistry graduate could better. Almost none of the large scale Western military actions in the last 70 years have been able to meet their original goals. The goals are changed to (something) and a victory retreat made ready.
No amount of technology will ever allow a military force to take and hold enemy territory if thousands of years of military common sense is ignored. You know, things like don't send endless supply convoys into enemy held territory that you've been fighting, unsuccessfully, to take for 10+ years. It's a pretty good bet they know you're coming, and that you'll obey the fucking traffic signs on the way: 'Uncle Sam Brakes for Insurgents' bumper stickers should be on every US military vehicle.
Sorry for the rant, it just pisses me off that we throw our soldiers (citizens) into war zones and actively undermine them by ignoring things paid for with millions and millions of lives. The recipes for successful war and successful business haven't changed in many millennia. War is pretty stupid, but if you're going to do it, go with what works and just do it. If you're a bit squeamish about the people dying in large quantities bit, maybe war isn't the path you should be on.