If you were a candidate in an election, would you prefer more support from voters or less? Put another way: would you prefer that your campaign staff persuade more voters to vote for you, or fewer? These questions seem silly, because of course you would want more support from voters. Surprisingly, when using certain voting methods it is actually possible for more voter support to produce a worse result for a candidate; such an outcome is a type of monotonicity paradox. In [1], we searched for various types of monotonicity paradoxes in 1079 single-transferable vote (STV) elections from a database of Scottish local government elections. The purpose of this article is to present in detail two of the most interesting elections revealed by our search. These two elections are arguably the most paradox-riddled real-world political ranked choice elections ever documented, perhaps rivalled only by four single-winner examples from the United States: the 2009 mayoral election in Burlington, Vermont ([2, 3]); a 2021 city council race in Minneapolis, Minnesota [4]; the 2022 Special Election for US House in Alaska [5]; and the 2022 District 4 School Director election in Oakland, California [6]. The first election we present is the 2017 council election in the Buckie Ward of the Moray Council Area, which demonstrated the most extreme instance of a committee size monotonicity paradox ever observed in an actual election. The second election is the 2012 council election in the Steòrnabhagh a Tuath Ward of the Nah-Eileanan Siar Council Area, which demonstrated upward and downward monotonicity paradoxes, as well as a no-show paradox. To contextualise these elections, as part of our discussion we indicate how often these kinds of paradoxes occur in Scottish local government elections.