If your buddy has a boom truck he probably can figure out how to hold a piece of pipe while unscrewing the joints. Odd to use steel pipe in 2007 for such a shallow well. To hold pipe as a safety when gluing or screwing, I use a few 6x6 pieces of wood, drill a hole through, split it on a bandsaw, heavy hinge on one end. Heavy clamp on one end makes it a quick action pipe grabber. Using two and leaving the couplers on the lower pipe means its pretty impossible to loose the string. I would probably just cut the pipe as it comes up, instead of going to war on the joints.
I would'nt try it with with much more than 4 sticks though. Its probably 1.25" pipe, and it deserves a better use as fence posts. Absolutely put it on 160psi poly or dedicated well drop pvc pipe.
15 amp fuse is pretty small for a 1.5 hp motor, especially with the quality of the fuses I have sometimes found. Go to a 20 amp breaker box. One good fuse now costs as much as a breaker, usually more.
A pump with a bad bearing from 2007 means you might be pumping the well dry from time to time.
Use a CRC capacitor start and run control box if its a 3 wire pump - motors run smoother. Next time there is a problem, you and your dog can have the pump out of the well in 5 minutes on poly pipe.
But remember the 800 bucks includes insurance if the pipe drops. Or get some more bids - this is a simple job in the extreme.
Also, 1" poly is adequate. Dean Bennet supply sells a poly pipe brass barb that is 1.25" MPT x 1" poly barb. Only place I ever saw that great fitting.