It depends on how you define unreasonable, but I feel like "Make a deal with Darth Vader, and then welch on it", "Fly a rickety old freighter literally into the Death Star", and "Cheat at Sabaac" are all objectively not very reasonable, but his goals tend to be things like "maintain continuity of city administration" and "make a living", which only become unreasonable in context.

Lando looks so much better by contrast compared to everyone he's standing next to XD

I consider Luke's most unreasonable goal and unreasonable method to both converge on Operation Save Darth Vader's Soul.