Good luck!!
I definately recommend covering a lot of it and doing one bit at a time -
There is a very similar plot on our site which has been taken on by numerous people - it is a massive meadow and no one seems to get beyond strimming it, digging a patch the size of a postage stamp and then giving up.
The current holders have strimmed it twice, but not got any further... they need black plastic!
My plot is a lot smaller and I'm just gradually reclaiming a bit more each year - on my third season I'm still only cultivating about half!
So be realistic, enjoy it and don't put your back out on your first weekend!
Sophie