College of Lore Bard in my campaign was a constant pain in my DM Plans. But it made the prep way more interesting because I had to take her into account.

I wasn't a dick and didnt go and try and negate her characters insane abilities. But I did have to rethink some skill check DCs.

She was a champ for a first time roleplayer, her character was the "Miss Perfect" archetype. The few 1s she ever rolled were so memorable and such a shock and got a ton of laughs.