I don't know what state you are in but more states are opening up raw milk sales. It would be hard as a family farm with one cow to pasteurize your milk to meet the standards. Just google raw milk laws for your state to find out. ND unfortunately can only sell raw milk if you own part of the cow. Like herd share. You buy a small part of the cow and pay for a portion of it's feed and then the actual owner of the cow gives you the milk. I have not done that.
I do have a 4 year old jersey now and a heifer that will be due in April. I do make cheese, cottage cheese, butter, whipped cream, sour cream, buttermilk, ice cream, and yogurt with the extra milk if I have any.
It is hard to tell you what kind of shelter you need when I don't know what state you are in. Most cows need shelter from sun, and wind. They can do fine outdoors in rain or snow. I do have a barn but most often they have a wind break on three sides with a roof, made out of metal. Important thing in winter is to give them straw or something to lay down on that will give them some insulation against the frozen ground. Remember you will have to have a water source that has a heater in it or give enough water twice a day. If you live where it is warmer you probably can get away with an area that provides some shade.
- This is there winter shelter.
You will want a stanchion to milk in, though, something that locks their head in place and hopefully keep them moving around from side to side.
My only experience with goats was when I was a kid and the milk to me has a gamey taste and smell. Remember goats will require you to have better and higher fencing and they will eat siding off of buildings, trees etc. They like to climb also and no vehicles can be left in there pasture. I don't have the money to either fence in an area big enough for them to graze in all summer or provide them with that much hay.
Depending on what kind of cow you get will depend on how much milk you get. I milk twice a day and then two months before I dry off, I go down to once a day, preparing for the dry off. During that time I still get about 2 gallons. At her maximum she gives me 6 gallons. A new heifer will give about 3 gallons for a jersey. Of course it all depends on genetics, grain, and hay. My son is getting married next summer so I need to get away and all my family will be gone also since the wedding is some distance, I will need to leave my cow for a weekend. I have not done this yet but lots of people have. I plan on leaving the calves on the cows and when the calf gets old enough you can go from twice a day milking to once a day milking. If you time your weekend of leaving right in their lactation (Calf older and they are past there peak production) you can leave for a couple days and the calf will be old enough to milk the cow out enough so she doesn't have ill effects while you are gone. So there are lots of options on how you milk.
I wish you the best. Good luck.