Warning - it's long!
So, after six months of fiddling around with it, we finally have our machine milker working. Our main issue was electricity - we were running it on the same breaker as the rest of the barn and it was overloading. We tweaked the system and the milker was working, but I took a few days to get the cow used to the noise of the pump running. Then I added in the noise of the milker itself. Finally, I put the inflations on her at the end of milking and got about a cup out of her. She stood really well and I was ready to go to town. The next morning, though, the milker would not develop enough vacuum to even bother putting it on her.
Knowing we still had electrical issues, we were going to run a new electric line and hook it into the same breaker as the clothes dryer, figuring that we don't need to run the dryer and the milker at the same time anyway.
Then it finally dawned on us that we can use the generator to run the milker. The gennie had been in storage for six months, though, and wouldn't work properly. It took another three weeks to get that back. I ran the generator, the pump, and the milker while I was cleaning her up...she was a bit tense and bug-eyed, but I decided to go for broke. All was working well, but then she shifted and the cups fell off. I ended up with half of the milk in the milk can and hand milking the rest. She has one light quarter due to mastitis earlier this year and I think the cup just didn't have enough suction.
I bought an inflation plug for that one and milked her with the machine again yesterday. This time, I got a gallon out of her with the machine and milked one quart by hand. Mostly because I'm not sure when I should take it off. I figure that within a few days we will be old hands at this.