Dang it, you're making me be serious.
My wife and I have discussed doing this. I know a guy who started raising grass fed 4 years ago. He is getting quite a reputation for his beef, so we are talking about buying a half a cow
Sample first, then dive in. Most will have a package in the freezer they can sell you. I prefer a great ribeye to a filet any day, I love the velvety texture and buttery fat. If I want to check overall quality I will ask for NY strip. They are the lowest grade steak (leanest) in a side, so if those are great you will be in good shape. Can't go wrong with a 1 1/4" thick Porterhouse, though...best of both worlds.