Of course I'm glad I did it! I love my cow and love being able to drink milk again. I get horribly sick from past/homogenized milk and hadn't used any other than for cooking for nearly 15 years before the cow was in milk. It isn't all outgo, though. She raises up a couple of extra calves for us each year and I don't typically milk every day because the calves are able to take enough (once they are big enough) that I can skip milking for a couple of days at a time. Of course, that means that I don't get much cream and I haven't made much cheese lately, but my time has been occupied elsewhere anyway.
However, even with that, the milk from my cow is more expensive for me than buying it in the store. I'm not doing it to save money, but to be healthier. Also to raise healthier beef for my family to eat. The extra milk and they whey get fed to our pigs and chickens, too, so no milk is ever wasted around here.
In the state of Wisconsin, it is illegal for people to share ownership of a cow and share the milk from her. Sad state of affairs in the "Dairy State".