Looking for some advice for our steep driveway

Unless there is loose stone and gravel on the pavement and concrete, this should be pretty easy on a dry day. Even wet should be fine. Don't try it in winter weather. You're more likely to damage something using a 2nd truck and tether if you ask me. Keep it tight and they need to track you, keep it loose and they might accidentally drive over the strap. As long as you have enough room to turn the corners, I say you're fine. A photo would be great.