About three months ago I decided to stop purchasing factory-farmed meat. It's been pretty difficult for a few reasons.
The biggest reason, by far, is access to information. Roughly, I would like to purchase only meat from animals that lived a "happy" life and had a relatively short death. Animals that lived outdoors, basically. But there are no credible labels or certifications for this, which means buying meat at the grocery store is pretty much impossible.
So I have to buy meat from a farmer. Recently I've been using crowdcow.com, but even there, the messaging seems to be all around _flavor_ and not _welfare_. Farmers will tell you what they feed the livestock, not how they treat them. So the best you can do is research the farm and hope their website isn't lying.
Another difficulty has been flavor and texture--pasture raised meat tastes more gamey and is much tougher than "normal" grocery store meat. I've actually found that I prefer the flavor of "humane" pork and chicken but not beef.
Lastly there's price. It's about 2/3x more expensive. This isn't that big of a problem, because we simply spend the same amount as a household and just eat less, substituting for vegetables. It does mean that I buy a lot more of the "cheaper" cuts, which require more skill in preparation. I haven't yet bought a pasture-raised ribeye--it's simply too expensive.
As for eating out, it's basically impossible. No restaurant I know where I live (Chicago) credibly serves only ethically sourced meat, as far as I know. To be honest I still eat "normal" meat when I eat out, although I have reduced my consumption somewhat. There are, unfortunately, some products of dubious ethical provenance that simply have no substitute, like fine cheeses and cured meats.
It seems to me like a huge opportunity. I would gladly pay 2/3 times for meat if I knew it was raised more ethically. In fact, that's what I think meat _should_ cost (and _all_ meat be ethically raised).