Point #7 seems weird to gripe about. It would be so plain-jane to dryly say and spell out every plot point all at once. The show had me in the dark most of the time of what the hell was going to happen, in a good way of course.
Because it’s corny? Contrived? Stilted? Not a logical way for people to behave?
…uhh so tell the bounty hunter all the details, and on the off chance he gets captured/interrogated, someone else not beholden to original contract could bargen with that Imperial dude for stipulations he didn’t want to be a part of.
Or given the lack of trust between these two individuals, there’s a chance the bounty hunter could bail out on the mission and decide to sell/leak the information, forfeiting the chance to claim the yadpole.