@JB
Because where he lives means he has to pay some union guy from his ISP, a hundred dollars an hour to take 4 hours to move his Ditch Witch a mere 30 feet through the ground. And really any time you dig around utilities, it’s preferable to call and have your utilities marked first. Here, we can do it with one call and they’ll mark all the utilities, for free. I’m betting it’s not going to be free in where he lives.
@Jerky
I honestly can’t promise that it will get through, but it should. If I were you, what I’d do is find one locally, so it could be returned if it doesn't work. Don’t go for the cheapest either. Get a brand you have some experience with and trust somewhat. Then try it. If it doesn't work you can return it and start looking for other solutions like signal extenders, but you may end up blowing “on the cheap” out of the water.