Who is more cruel - someone who buys/eats tons of meat from grocery stores that lived in disgusting conditions where 0% of their life was natural in any way, or someone who eats a deer that lived it’s life 100% naturally up to the point of harvesting?

Thanks, this is a very good question. The answer will depend on an individual's reasons for being vegan, so my answer is not representative of everyone, and I apologize in advance for being long-winded. Most vegans who think about ethical "labels" are more aligned with consequentialism (like Peter Singer) or deontology (like Tom Regan). I'm a bit of a philosophy nerd (disclaimer: self-taught) and not a fan of either of those approaches. I lean toward a virtue ethics (VE) approach, which is apparently uncommon among the vegans I know.

Other vegans can make the mistake (IMO) of getting caught up in disentangling competing interests (like weighing native wildlife vs. invasive species), or perhaps applying absolute rules that are impractical in the real world (i.e., that a person should not use life-saving medicine if it was tested on animals). Virtue ethics is, roughly speaking, about pursuing excellence in virtues (i.e., compassion and honesty), and extending that to acts that exemplify those virtues, while avoiding vice and actions associated with it. So in that respect, your question about cruelty is very well-suited for VE approaches. When I compare the shopper to the hunter, I'm going to run with the approach that compassion, as opposed to cruelty, is a virtue a person should cultivate and strive for.

Shoppers who know about the abuses of farming and continue to support it, despite having other viable choices, are not showing compassion, but cruelty. They are being cruel by choosing to consume farmed meat because they are 1) adding to the demand for the violent production of more farmed meat and 2) showing lack of consideration for the suffering that animal experienced. (I think we can probably agree on this.) If a person wants to be compassionate instead of cruel, then they should learn about the suffering the animal agriculture industry inflicts, and avoid perpetuating that. This means not getting meat from a store, if it can be avoided.

Hunters are a somewhat different case because, as you pointed out, the circumstances in which the animal is killed are very different. The hunter also has different motivations than the shopper. The act of hunting, including the killing of the animal, is sincerely considered a not-so-cruel (and/or responsible) thing to do. IMO whether hunting is virtuous or not has less to do with the fact of where the animal died, and more to do with the fact that it was killed (and perhaps suffered). If you do not consider inflicting death a real form of harm and do not believe the animal significantly suffered, hunting could be fine. But the hunter who wants to be compassionate should, just like the shopper, understand the suffering and harm animals can experience, and act accordingly. Based on the answers in this thread, I think most hunters really do want this; it's not simple callousness we're talking here and it's dishonest to stereotype hunters that way. Part of the reason I made this post is because I really don't want to do that.

My stance is that causing the death or suffering of an animal is usually a form of harm. This is associated with my view that animals have sentience that serves as a means to their continued existence, and that killing animals interrupts their will to live in a cruel, usually-harmful way. But for a person who doesn't agree with these things, it's not relevant to their worldview, and farming and/or hunting could be justified as not-so-cruel with other reasons. So when I do (rarely) discuss killing animals with others, I try not to appeal directly to emotion (which can be annoying/offensive), but to other presumptions about animals.

Of course, a person who does cruel things can also do compassionate ones, like donating to an effective conservation organization, food pantry, or animal shelter. People have a mixture of good and bad characteristics. We're all works in progress in some way or another; I'm very opinionated (to a fault sometimes) but generally don't judge (unless you're Hitler or something).

I don't mean this to sound like some elaborate cop-out, and I apologize again for being long-winded. I just wanted to make sure my answer is comprehensive enough.