Your well might be 580 feet deep, but your static water level is only 60' down? Can't imagine then that they would have set your pump 580' down in the hole. Regardless of that though, you're pump will still only be lifting the water with the pump the distance above the "static water level"... so around 60'. Pretty much any submersible won't have any trouble doing that. The 200' rise to your furthest waterer potentially "could" create enough "back pressure" to never allow the pressure switch to turn on (because with 200' of rise in a pipe full of water beyond the pressure switch, the pressure at the pressure tank ought to be measuring around 92#.... .46#/foot of rise)! So the pressure switch probably wouldn't be expected to ever kick in to turn on the submersible, if you actually did get water up to that waterer. I'm surprised you ever had water at the waterer at all, without a secondary lift pump to get it there.
But of course, you've indicated that you have disconnected that now. Does that mean that you've closed a valve where that line leaves the pump house/pressure system, or that you've shut it off up by the waterer at the top of the hill? If you've not closed a valve where that line leaves the pressure tank system, the weight of the water in that line is still pressing down against it, and it will likely act as a "mini-pressure tank" (albeit with limited volume capacity) on the system. At the very least, it will generate significant pressure against the pump when it needs to run.
It'll be interesting to hear what the well guy has to say about it.