I guess what I look for in a cow is someone who's interesting and keeps taking us by surprise. I get bored with a lot of lolcows because they really only have one issue and there's only so much they can say about it.
I'm not a fan of the cows who are mostly just unfortunate - if I feel sorry for them, it's difficult to laugh. For the same reason, I find the ones with legit mental illness uncomfortable to laugh at. Gail Shuler (sp?) is fascinating, but she's also in a horrible situation with her mental state. So the cow has to be kind of an asshole.
But conversely, I can't laugh at someone like Nick Bate - not that he doesn't deserve it, but because he's just too awful. Molesters and abusers aren't funny to me because other people suffer.
I don't know, maybe it's the SJW in me, but the lolcow has to inhabit a very narrow band in order for me to be interested.
I don't really laugh at Nick Bate himself, because his stupid antics, like the Kentucky thing and saying "oot" all the time just piss me off in the context of what he does. However, I do take relish in the horrors that will be inflicted upon him as part of the rest of his new, very limited, very painful, and likely short life.
But I agree more or less with this idea. Sarah Butts, for instance, is more of a ragecow than a lolcow at this point, and I follow that more because I hope that situation will change than anything.
I find Phil/ADF is basically in the Goldilocks Zone of awfulness Chris used to be in. He's a terrible human being in pretty much every respect, and his antics are shitty and disgusting and full of fail enough to be hilarious. However, he's not atrocious enough that being pissed off at him outweighs the fun of laughing at him, and he's not sympathetic enough that you can really feel any guilt about laughing at bad shit, almost all of it self-inflicted, that happens to him as a result of his shittiness as a person.
The only lolcow I can truly stand is Chris, because he's so stupid and odd it's both hilarious and ingenious, the others just piss me off. Maybe because Chris was my first exposure to people of this type, so I'm desensitized to the others. I've laughed all I could at America's favorite autist, and I still do, his stupidity is almost endearing.
Bad art has always been a hobby of mine. So, I tend to gravitate toward artist and film maker cows. I love the bizarre worlds and stories that come out of their weird little minds. Probably comes from being an artist, myself.
I wouldn't say "dislike," but I've met potential lolcows who are nice people at their core. Some have even become my friends. Part of me wants to share their more ridiculous actions and qualities, but I'd feel guilty.
So, it helps that many lolcows are kinda people that you just can't feel sorry for, much less feel sorry for laughing at.
My favorite cows are the ones who draw shitty art that I can lol at. It's especially lovely when they develop a romantic obsession with some cartoon character or when they draw really bizarre shipping couples.
I don't want to appear to be sucking up to the admins, but I firmly agree with @Null and @Hellblazer - anomalous individuals whose behaviour mystify and require some sort of explanation are best. Also, as someone very much into cultural history and the concept of culture (that is, the passing down of information from one generation to the next), I find the way certain lolcows obsess over pop culture and then filter it through their own unique lens to be totally fascinating. Exactly how did we, as a society, reach a point where grown adults choose to dress up as incontinent biped animals? Where they see fit to create media concerning flatulent underage pregnant horses? Yes, such phenomena can be explained, but - for myself, at least - that doesn't detract from the sheer oddness, the mystery of it all. I should add that this is why I could never get into the sluthaters or SJWs as a whole. Men blaming women for not taking an interest in them are easily explainable - to the point of being axiomatic - and teenagers playing hunt the identity and doing their absolute best to convince themselves they're somehow unique have always been a thing.
Something else I feel makes a lolcow compelling - the possibility (however slight) of redemption. Or if that's too strong a word, improvement. Granted, I'm a huge fucking faggot someone who always wishes to see the best in people - but I'm also objectively interested in seeing if there's the possibility of an evolution of some kind. It's why I'm rooting for Chris and was delighted to see Kengle grow a pair and put that absolute fool Shaner firmly in his place - and why I follow Dobson with the same fervour usually reserved for tabloid celebrities. A man of reasonable basic skill and talent committing a long, drawn-out professional suicide (one you know he could avoid if only he could develop a decent work ethic) is a gripping thing to witness. TJ Church on the other hand - you just know he'll be arguing with his detractors on his deathbed.
Fave lolcows (My choices will probably contradict everything I've just typed, but never mind):
Leighanna (the sperg's sperg of choice)
Hayden Black and Julie Goldstein (incredible to see so much effort expended on something so dreadful)
Preggo Apple Bloom (edgelord kids and little more, IMO - but still utterly bizarre
...EDIT 15/10/15: My apologies. Turns out I was very wrong. )
Like some of you I don't really like the tumblr/sjw kind of cow; while they're stupid, self righteous and disconnected from reality to the point of being amusing they're not really 'fun', they're just cringeworthy. I mostly lurk that board for bias confirmation.
Another the thing I don't like about them is that they don't live in their own batshit insane little worlds, but they're just cogs of a bigger machine of idiocy. People like Chris are fascinating because they have their own brand of lunacy, nobody sees the world trough the same lenses (or rather kaleidoscope) as he does.
I think the lolcow that’s entertained me the most is Robert Wayne Stiles. The cave story stands out, but even then there’s just so much to laugh at: his high school anarchism, the saga with Crissy Moran and run-in with the FBI, his brief friendship with ADF and his gang, the coprophilia, his misadventures as a harlot, the attempt to get /mlp/ to be his personal army, the twisted relationship with his parents, the obsession with Bioshock’s Elizabeth. It’s an epic that rivals Homer.
Hmm, I'm finding I like lolcows who are both bizarre and have some bite to them. The Lolcows who pick a fight or try to troll their critics are definitely the ones that catch my interest, and the ones who are edgy, bizarre, and have that certain something that makes me howl in laughter as they try to talk shit and insult others.
I'm also partial to the more extreme MRA and incels who just are so over the top and ridiculous with their ideology that it makes them more a caricature than someone who is actually offensive. Marjie is a good example of this kind Lolcow.
My most consistently watched Lolcows are actually the religious zealots from the American Christian Right. I keep loose tabs on several who are so bizarre and over the top that I'm often amazed at the stuff they produce. David J Stewart, Anna Diehl , and Pat Robertson are pretty good examples from offsite.
I like lolcows that are oblivious. Lolcows who are engaged with the popular culture don't do it for me as much. I prefer straight-up surrealism. However, Mr.Enter is a guilty pleasure cow for me, because he's quite accessible.