On one hand, I really don't agree that "being awesome" in a game, especially sandboxy games like Hitman and Assassin's Creed, shouldn't be something you have to earn. I know that, for me, pulling off a really elegant kill in Hitman wouldn't be even slightly as satisfying as it is if I hadn't had to work out how to it myself and put the work in to do it.

That said, the flag task is a) just completely dumb and b) a real shame when you think about how sandboxy the rest of the game is. I get similarly irritated when the GTA games throw in ridiculously difficult missions on the main plot strand; in my view, if something is nigh-impossible, it ought to be relegated to the side quests. I honestly can't think of anything in any of the Hitman games which railroads you to that extent, and which so comprehensively shatters the illusion that you are playing a game. Hell, it doesn't even make sense in the context of the game - you're a descendent of the actual assassin who's being interrogated by some conspiracy in the near future, right? What's to say they can't say "Fuck that, we don't care about the silly flags - we'll fast-forward this bit".

Maybe you should check a walkthrough and see if you can't just track down the villain and kill him without getting the intel.

(Incidentally, I really like the way that Dragon Quest: Journey of the Cursed King manages to sidestep the "Do It Again, Stupid" problem - if your entire party is killed, you lose some gold, but you keep all the XP you earned, so the battle which killed you will probably be a bit easier when you get back to it - especially if you make a habit of buying the best equipment that you can afford every time you go back to a town, so that whenever you set off adventuring you're reasonably low on gold - then you're not gambling too much and will probably still be ahead financially after taking the hit for dying.)

Clarification: I should point out that I don't actually like Do It Again, Stupid play either. The cool thing about Hitman is that if you aren't clever enough to spot the optimal way to complete the mission, or skilled enough to pull it off, there are still alternative methods available, and you can in fact improvise your own technique, which can be as subtle or as bloody as you like. Even though you don't get as many rewards for openly gunning people down in cold blood - you get less money, and in Hitman: Blood Money your notoriety goes up (although you can replay missions or pay money to make it go back down) - you can still progress. I kind of wish the GTA games would incorporate something like this (say, offering easier missions to get around a particularly tough mission in the main plotline, but at the cost of morally compromising yourself, or losing credibility with your gang, or getting a suboptimal ending), and I'm slightly disappointed that Assassin's Creed seems to have deviated from the sandbox model offered by Hitman - assuming you can't just track the target down in a different way.

Just an edit to this: I have now completed the pointless flag question of tedious doom (so I am not just Shit At Games TM) - and it was actually pretty easy but the PRINCIPLE of the thing remains.

And also to add a clarification to your clarification: by 'be awesome' I sort of meant give you an array of skills, options and abilities that allow you feel that you are - rather than actually mollycoddle through noticeably dumbass behaviour. The point about Hitman is that the character is generally all tooled up with awesomeness at the beginning - your target doesn't wander up to you half way through the game and ask you to make him a cup of coffee (or if he does it's an opportunity to off him).