I've also considered going ahead and cutting the whole in the wall, putting in a low voltage box, and getting the fish tape where all you have to do is tape the wire to it and pull. That would be easier than him having to drill through the floor. But we get back from vaca the day before that so not sure if I will have time.
That's a good idea. If it's easier, he's likely to do it for nothing.
BTW, typically installers never use low voltage boxes....just a wall plate screwed into your drywall. So, if you want it done right (using the box), you may want to do that pre-work yourself.