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Trying to make sense of Star Wars is like trying to make sense of Bernie Sanders.
Sure, you might be able to do it, but is it really worth the trouble since you know the answer’s stupid?
Since Luke did that little wave to R2 before he went off the plank, I would guess it all went according to plan.
It was a Indiana Jones plan, made up as he went along.
Best guess..
Luke’s Plan A: Plant Lando and Leia as spies to get him as much information about Han (where he’s being kept, who’s in Jabba’s court, etc.). Get into Jabba’s palace under the pretense of offering the droids as a gift. When near Jabba, use the Jedi mind trick to get Jabba to release Han. Everybody GTFO of there the first chance they get.
Luke’s Plan B: Get as much of the team out as possible with guns, lightsabers… whatever is required.