From what i have seen so far, it would be pretty hard to mess up all of the things bethesda has shown us. Maybe im just an optimist, but it seems like they have really listend to the community and are going to implement our ideas into skyrim quite elegantly.

On the other hand at some place they told that quests are dynamically arranged in dungeons that you have not met yet, which is great, and are tailored you your character's strengths and weaknesses, which is not bad if implemented correctly, but do we have quests that force us to retreat and come back when more powerful and prepared?

That's the question that is very important, because if we do not have such scenarios of initial failures and final conquers, advancing in levels would be meaningless, like in Oblivion, unless gaining new perks and skills for our specialized character in higher level, change the game-play so drastically to keep it interesting for us to want to advance to higher levels, in order to gain those specialized perks

why does everyone forget that detail that makes it so different? this ONLY applies to RANDOM QUESTS!!!!!
the main quest and probably the guilds too, are going to have a similar leveling to what morrowind has