I wonder... so many "what if" can happen in the plan. This is especially true with the Leia/Chewie part.
The recon action of Lando I can understand, and would probably work all fine. (and yes the comic about him gambling his way into the local population against a hutt lord is cool)
The Negotiation with the droids I can understand also, well droids are easier to bail out if negotiations would actually work, esp with the help of Lando, and lightsabers can be rebilt, so no biggie there. Though I think Luke would benefit from a backup lightsaber on his person.
Even the scene where Luke deals would Jabba would make sense, if he did not drop by with the Rancor. (I assume he did not plan on a rancor visit)
But really I don't see the point of the whole Leia/Chewie thing.
And I do understand running in killing everybody would be the good and effective sith way, but unfortunately Luke did not see the virtues of sith teachings yet.