The only way I can think of dairy being "humane" is if you rescued a pregnant cow, and allowed the calf to stay with her and just took small amounts of milk from her, so that she had plenty leftover for her calf (milk production would increase to meet demand up to a certain point). But even this assumes that animals are here for us to use, and that is not really the case.
Organic farms still remove the calf from the mother, and male calves will still become veal. The cow will still have a shortened life span and be slaughtered for her meat at the end of her life.
But buying organic dairy, even if it were humane, would not solve the 'convenience' factor. Most restaurants do not offer organic foods. It's quite easy to replace dairy at home with soy, rice, or other plant based alternatives. The one thing most people have a hard time with is cheese.
I think being vegan is only as hard as you make it. It's a bit of a shock at first, but it is certainly do-able. Any major change in lifestyle is hard at first but gets easier with time. I'm not judging vegetarians who consume dairy - I was one for ten years! I always thought veganism was too hard, and that it was ok since the cow wasn't being slaughtered for her milk. Once VB
(and other sites) opened up my eyes to the inherent cruelty in milk production, I couldn't imagine doing anything but giving up dairy. After that it was easy, whenever I wanted milk I thought of the veal calves and couldn't bring myself to drink milk any more than I could eat a piece of steak.
Yes, it is a journey, and it isn't all or nothing. Every little bit helps. we all strive to do the best we can and we all have room for improvement in reducing cruelty. However you get there, and wherever you go, I wish you luck
ETA: I agree that this should be moved to the vegan forum.