I've been trying to come up with a good word to describe the attitude I think Oliver Queen takes to heroing and life in general, and I can't quite seem to find it. "Half-assed" doesn't seem quite right, neither do "arrogant" or "indifferent", though they both play a role. He reminds me of that friend you might have that's always starting projects, but never finishes them. He lacks follow-through, whether due to laziness, lack of planning, or whatever.
When he wants to jet off with the Skylarks to Alaska, he comes up with some nonsense about all his employees working at home, because it will stimulate creativity and save fuel since people won't have to commute. Because certainly people who work for an engineering and design company are going to have the equipment to put together prototypes of their potential doodads in their own homes. But he doesn't care because he's too wrapped up in his Arrow stuff.
Should he concerned about flying off to who knows where with three triplets who first attacked him, then proclaimed their love for him while finishing each others' sentences? Probably, but Ollie doesn't give it a thought. Some of that is certainly ego, he figures he has them wrapped around his little finger (because he's such a stud, natch), and some of that is he figures he can handle them if that doesn't turn out to be the case. But there's a general sense that he just doesn't stop to consider whether this is a good idea, if there could be ulterior motives, nothing.
Even when he learns two of the Skylarks are endlessly devoted to their father, but one seems to legitimately like him, Ollie doesn't bother to come up with some way to tell them apart. Even though it'd be helpful to know whether the Skylark he was with is the helpful one or not, he plainly states he doesn't care. Which is how he gets lead into a trap, and convinced the Good Skylark sold him out. If he had bothered to slip her a tracking device, or a special arrowhead or something, he'd have known she wasn't the one he fooled around with the night before, but he figured he had it under control. It's creepy enough when Leer doesn't care to distinguish between his daughters. He's the bad guy, he's egotistical enough to believe it doesn't matter as long as they serve him, fine, it works. For the supposed hero to not care, you get the feeling they're all faceless extras in Oliver's own little fantasy world.
Which obviously, he didn't. He may have destroyed Leer's gold mine with the help of the locals, but Leer escaped with the daughter Ollie rejected (because he didn't devise a way to tell her from her wicked sisters). The other two Skylarks escaped separately. If Leer did what he planned his creatures have been set loose into the wild. I'm not seeing how Ollie can say he saved the world here. I'm not sure how the townies will get the gold now that Oliver blew the mine up, but if they can, how is that going to be any more environmentally sound than when Leer was doing the digging? Maybe they won't use cyanide.
The blood and the bear are the real kickers for me. Ollie struts into town making this big deal about wanting his bear (the one that Leer set loose in issue 8), makes a deal with the locals for it then forgets it until it's too late to go back for it. For all his insistence it was important to get that bear out of nature before it messed with the ecosystem, he forgot it except when it was too late. Likewise, he doesn't even think of the fact Leer can add his blood to his collection until after it's all over. Never mind Leer's had his blood since the Skylark's modified hummingbird yanked that mini-arrow out of Arrow's face in issue 7. That whole time Leer's had his blood, and it only just occurs to Oliver now.
What's that say about Oliver Queen? I don't think it's that he doesn't see the dangers he's up against, or the importance of stopping them. He seems to get that, but he doesn't keep it in mind. He lets other things distract him too readily, whether it's inconsequential stuff like making out with the attractive girl, or some other smaller problem, which he then forgets about when the next thing pops up. He forgets about the girls stealing his blood and faking his death because they sic wolves on him. Then because he's met Leer. Then he gets distracted from Leer's bio-engineering because a bear's loose. Then he gets distracted from the bear by Leer's mine, and then the whole thing with Skylarks distracts him again. He's like the Tick: easily distracted by shiny things, and he's in a world full of shiny thing.
Maybe it's as simple as realizing it's OK to enjoy being a costumed hero, or a CEO, but there are people counting on you to do it well. Which is the old "great power comes with great responsibility" saw, but I'm not convinced it's as simple as that. I think Ollie gets that, he just doesn't always follow it. So maybe half-assed was the right word. He has to understand he can't halfway do these things. If he wants to run a company, then he has to really run it, even if that only means making sure the people he asks to do it in his stead have the authority to do it properly. If he wants to be a superhero, then he has to concentrate on it. Think things through a little more, stop counting on charm (which he doesn't have nearly as much of as he thinks) to see him through.