I'd like to know something. It's got me a little concerned.

Right now, I am milking Grace in the 7th hour of the mornings 5th hour of the evenings... when winter hits though, what times should I do? By 4:30pm in November/December it's already dark, and I don't plan on trucking through the yard to grab her. Should I get up earlier? And when should I start adjusting the time? Is it a big deal? Or am I making this more than it has to be?

With milking her twice a day, the morning milking being the longer fill (7am-5pm=10hrs....5pm-7am=14hours) you can likely start milking once a day once the days get shorter unless she's a good producer that would get too full with milking once every 24 hours.

When I cut back to once a day milkings, I cut out the 4:30 am milking and milk at 4-5 pm.

Don't know your set up, but mine come to the house twice a day and beller till I go out and milk. I don't have to go find them. Occasionally I have to call them if they are not right up here, but they know their names and come.

They are out in the pen a few yards away, I have to go get them and bring them to garage where the stand is at, at least until we build a milking station

It didn't occur to me that DST would be adjusted by then, meaning I'll be adjusted to Summer's 7am when it's Winter's 6am, thus I can milk her among the 4th hour at night Just before dark! \o/