On the reasons not to attempt the retrieval, the possibility that trying might block the well irreparably would be high on my list. Drilling a new 500' well isn't going to be cheap anywhere.
Using
@LouNY's pipe numbers, it would seem that the lift is on the order of a ton; 1500+lbs of pipe, 80lbs of water in the pipe, 110lbs of wire, and a hundred pounds or so of pump. Oh, yes, and the safety cable. You'd also need the well head clamp for the right sized pipe, and the winch to pipe adapter, and the 4-8' pipe wrenches need to unthread 25 year old pipe. Plus of course, the grapple capable of lifting a ton safely, the 25-30' winch tripod to be able to lift a 20' section clear of the well head, and the winch that is capable of safely lifting that much weight without overheating.
All that I am saying is that to me this is a little more involved than snagging a lost fishing rod in a pond.
All the best,
Peter