It would always be a worry leaving them out so far from home, unless a friendly neighbour would keep an eye on them. Where I lived previously I was at work all day, the goats were kept inside. They were out at all other possible times. Even now the goats are inside most of the time, unless weather is dry (or reasonably so). autumn 2012 yearlings did run out 24/7 with a field shelter, but well fenced and I could see them from the house.
for milking I just bring them out of the pen (inside a bigger building) and have 2 half pallets stacked as a milking bench, goats tied by a lead to the outside of their pen.
Is there water supply on the land?
MY 2 yearlings (ToggxB.Saanen) were reared on their mums but still love attention so much they leave their food while I scratch their heads, - helps stop the fighting over the last crumbs in a bucket

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Is there water supply on the land?
What do you mean strip her down? milking her out? I suppose if she only has one kid and that only feeds from one side, if she is a good milker there should be a decent amount from the other side. If that works then thinking about it you may not have to seperate them ?
Luckily you are thinking in advance so it gives you time to try and get round some shows this summer, don't be put off by how posh they all look, there are different levels of goat keeping, as long as goats are well fed and happy, they don't have to look the cream of the crop. :-)
I think on the defra website there will be a section on welfare of goats, and there is one on the RSPCA site, it may be worth having a look at them.
There should also be books in your local library, even town centre libraries. It's always good to read a book, they answer the questions you don't know to ask, and it helps to keep libraries open!