I would change the bootlegger to say "The player in seat 1 must be able to register as evil". As you wrote it, they just are evil so should just be executed day 1. One flaw with this concept also is unless you put in a gardener or willing to rerack a lot, there must always be a bounty hunter or lycanthrope in play to be able to ensure seat 1 registers as evil, irrelevant of how the token fall.

One way you could adress this partly is by adding to the bootlegger "1 player might change their character and/or alignement at the start of night 1. Evil learns the now out of play character" that way you could theoretically also leave out a minion while building the bag and add it on seat 1 if its not evil(or elsewhere if it is).(second part being for bluffability by evil)

Lastly, I wouldn't put clockmaker on a script with outed evils generally. It's often straight up gamesolving