YES WHY. Stories have beginnings, middles, and endings. Villians in the 2nd act can be heroes in the 5th, but the audience has to see them experience an accounting of their crimes and errors. It's also important for the character themself to experience the bounds of their limitations and to be confronted with what it is they owe to higher powers, whether that be identified as earthy constructs or heavenly systems. There are stories where exceptions can be tolerated for the fool/jester archetype, characters whose performances are generally unbound to societal expectations, but if a character has been driven to conform and invested themself poorly in "popularity" over ethics or morality, earthly accountability is usually the kindest of resolutions to their "irresponsible" behavior. This narrative need for accountability is often compounded by the characters relative position to power, greed, corruption, their ability to influence others, among other societal ills.

Listen, everyone makes their own choices and they are accountable for such. If they are too scare to take good advice because it may make things awkward, or uncomfortabke, or complicated for them, then they get the privledge of dealing with the consequences of their own decision making. That said, there is a pretty obvious pattern in all this, I mean this isn't exactly the best timing for cigar-filled backrooms or shadowplays. If something incongruent to the rest of the story or lore happens, the nerds will notice and you'll hear them nitpicking the details at conventions and message boards. The buck has to stop somewhere afterall.

You have to use atleast three out of the five on the table. I'd favor discarding the lower cards, but I'm not sure if its a rule that you have to.