Masquerade - S2-E7
Plot hole: Why did Stefan and Damon suddenly decide to abandon their plans to kill Katherine when the spell linking her to Elena were broken? When only moments earlier, Damon said "The second the spell is lifted, I'm gonna drive a stake right through your heart." So that begs the question why did he never follow through? Why instead place her in the spelled tomb that you know can be dispelled? It makes absolutely no sense when you think about it.
Plot hole: Bonnie is the anchor for the other side and feels when supernatural beings die. How come she didn't know Katherine wasn't dead? Did she never think it was suspicious that she never felt Katherine's body after she died?
Suggested correction: Katherine died but didn't go to the other side. So she didn't need to go through Bonnie. She went to hell to Arcadius. Bonnie is not the anchor to hell, we don't know how going to hell works.
After everyone finally realises that Elena had been possessed by her Doppelgänger Predecessor, It is actually shown that Katherine were more or less dragged away from Bonnie before she could crossover to the Otherside. So we do have some idea as to how one ends up in Hell.
Suggested correction: Katherine was a human technically when she died.
Technically, she was supernatural because she was a doppelganger, so she should've gone through Bonnie.
And even she was a traveller.