His well was drilled with a cable (spudder) rig. Drilled is the wrong verb, pounded is more accurate. The hole is very crooked, a drill rig will get stuck so nobody will try it. It probably has 20 feet of metal casing at the top. Bailing is dropping a tube down on a cable, grabbing some sand then pulling it back up, empty out, do again. Very time consuming when 300 feet deep. I think Chris said when the well was sunk it took a month. If the driller says the well's done it's likely done.
Start @ 4:00 to see how it "drills". @ 9:40 he bails it out.