1. I don't think I'd be too bothered if they genuinely can't afford it... which reminds me I probably should register my Atari ST copy of Llamatron sometime soon, as back when it was current I couldn't scrape together the £5 cost (I was a child, not in a position to have any kind of paid work, and my parents wouldn't pay for it or give serious pocket money) so just kept on playing through the shareware warnings.
If they're someone who obviously can afford it but just likes getting stuff for free, it's maybe a different matter.
I'm a bit confused by the question being asked by a (presumably american) college student, as I certainly didn't have the kind of money required to be that morally picky when I was there. After rent, tuition, normal living costs and some semblance of a social life, there wasn't a great deal left. I was without transport when my bicycle was stolen in my first year until the insurance payout came through, and was king of the goddamn world with my cheap and nasty car in the third year, having worked my ass off all summer to afford it. And this was even with some support from ma + pa and a generous great aunt, and not going on lunatic clothes shopping sprees like some of my contemporaries. I had the stereo which I'd had since I was 12, and a scrappy hacked-together PC, on which were played the handful of albums and singles I actually owned, and an about equal number of P2P'd mp3s (burnt as audio on super cheap CDR with an ancient burner) and copies. If we wanted to see films, it was usually collectively around someone's small TV if it was on-air, or they had the VHS or (ooh!!) DVD, which I think is itself illegal as it counts as a group showing (the times that some larger group booked out a lecture hall to show a rented movie definitely were illegal, even though they didn't charge admission beyond chipping in to get the renter a drink). When I finally managed to stretch to a DVD player of my own - size of a mediaeval castle and about as primitive - the majority of material that went into it was on homemade VCD from P2P DivXs. Just so I could chill out on the bed watching it on a "proper" (14 inch, mono) TV, rather than hunched up at the computer desk (and its 15" monitor and stereo speakers).
My legal audio and movie collection is a lot larger now, and I buy actual books rather than downloading cracked ebooks, but I still remember being in that position. I already ended my days there right up against my credit card and overdraft limits, eating 10p noodles cooked in a travel kettle (and driving back home, at last, at 50mph to eke out the last of the petrol, praying that my unreliable fuel guage didn't let me down halfway as I was nearly out of pay-as-you-go credit for my craptacular cell phone). I simply didn't have the budget to buy anything else. Studying already took up more spare time than I had (one big thing that I didn't really pirate at college was games, despite having done it a lot at school - someone gave me a cracked version of halflife, I had a few rounds of halfhearted counterstrike and that was it... couldn't afford the time) so getting a job during the semester was out of the question. Cinema trips were incredibly rare. Concerts, right out. Our TV and radio signals were horrifically bad. The entertainment had to come from somewhere (NB, this was before youtube et al)...
2. A large proportion of moviegoers are idiots, it would seem. Though if they enjoy what they go to see, who are we to try and force them to do otherwise?
Personally I wasn't massively impressed by Scott Pilgrim. It was an alright film and something a bit different, but felt rushed and didn't stand up to the hype. Apparently it's not the best representation that could have been made of the source material, largely because they've squashed seven editions of a comic book into a single 2-hour film, and that rarely goes well. If it was a touch longer (maybe with an intermission) and had some of the supposedly missing exposition restored (e.g. how is this limp streak of piss so good at beating down random hard cases? Oh actually he's a locally reknowned streetfighter as well as being good at DDR... yeah that didn't make the cut) it may have been a bit more enjoyable rather than a long parade of SFX and non sequiteurs, and word of mouth may have supported it more.
I might yet give the comics a go. If they're "better" than the movie, after all, it won't be a total waste of time.
3. At a guess, i'd say "Kick-Ass did" for the first pic, and "what's the problem with that? it looks a bit cheesy, but a man dressed up in red and blue spandex with shiny silver eyes running around new york always will" for the second.