You have a most interesting project at hand. I believe Packard was the first to offer auto AC. It is a shame that you want info from us but won't take a few minutes to resize your pics. I am of the opinion that the expansion valve will work as is. There are several other highly knowledgeable techs o...

From what you describe it sounds like they did OK.
Evacuation/recovery of refrigerant of a system with a pro machine seldom removes much oil at all.

Were you able to see any 'wet' areas on any fittings or hoses? Or areas where dirt had collected? (leaking oil tends to attract dirt)

"Do you think it was getting damaged by running it with such little refrigerant? "

The refrigerant carries the oil all through the system. Of course, only the comp needs any oil. So, yes a comp can be harmed by a charge level that is too low.
As you stated, only time will tell

send Tim an email with the make model year of car and ask him for everything from the firewall forward. He will respond, he is very accommodating. Then you can compare your prices. But he has very good quality prices at very reasonable prices. This type of repair , while aggravating, and costly, is ...

"I saw videos of people flushing ac lines with carb cleaner..can I save some of the lines by doing that?" This yields very unpredictable results. My good friend John, above, probably has more faith in line flushing than we do, we just replace them. I do not think carb cleaner is a good cho...

"When I turn the center shaft by hand it is tough, it turns about a 1/4, the gets tight, I hear/feel a click and then it turns...over and over again." Bad news. "I'm thinking maybe the compressor went bad and then caused the clutch to break off. " Correct. How many miles out of c...

"Maybe he needs the money for the new car payments/full coverage insurance"

Clearly a joke. Get a bicycle

5 dollars gets you all of them, then you can figure it out. Cheaper than 13

Tim, ever hear the expression about beating a dead horse. I'm out

I got that.
Re-read what I wrote. New doesn't mean anything anymore, clean them.
I suggested you try a different pump, you ignored that suggestion.
All you did was repeat what you already posted