350’ of 1 ¼” pipe, full of water, wire, and pump is going to be heavy and slick. If you can pull it up 20’ at a time, you can clamp at the couplings, which is much safer. If a clamp in the middle of a joint slips, the pipe will slide down quickly and break the coupling off the top of the joint. If you drop or break anything, it would be less expensive to pay someone to pull the pump. If you don’t drop or break anything, you will save a lot of money.
You can also pull the entire 350’ out in one piece. As long as it is not very cold, and you don’t bend the pipe very much at the couplings, you can lay all 350’ out on the ground before taking anything apart. Two or three guys pulling up on the pipe and wire, while another guy takes the well seal and top joint across the yard 350’. Standing in the back of a pick up truck while pulling up on the pipe will help keep the pipe from bending too much as it comes out of the hole and turns to the right. Just want to make as slight a bend as possible.
Might be better to pay someone to pull out the old pump. Then go back with poly pipe and set the new pump yourself. Break the pipe, drop a tool, a nut, the wire, or anything down the hole and you will probably need a new well. Sometimes trying to save a few bucks can cost you dearly. I think everyone should try it at least once. You will learn a lot. Maybe the most important thing you will learn is that a pump mans job is not that easy. And when you consider all the liability involved, you can see why pump installers charge what they do.