Leia as Luke's sister is the biggest continuity error in the films and really causes the biggest problems.
As I said in the previous post, I'm pretty sure Han can tell what kinds of ships they are on the Falcon's radar. I'll have to rewatch it and find out, but I'm pretty sure he distinguishes between them when either the two Star Destroyer's come up behind him or the TIE fighters come after him the dog fight.
And if you agree with me that the Imperial Shuttle doesn't have a cloaking device, then the only explanations availble for Han not seeing it arrive just before he did is that his radar stopped working or there is a timeline problem.
The officer said it, he could be wrong, but by saying it, you create a 'law' in a movies universe. The break that law, you have to provide a spoken or shown instance in which this law is contradicted. This is a problem with alot of the continuity errors between the 6 films. Some you can explain because the 'law' is elaborated on, others (Obi-Wan once thought as you did) you have to stretch to find a viable answer. You can do the most outlandish things in a movie, but once you set up the 'laws' of that world in which the movies takes place, to keep the audience believing, you have to try not to break those laws. Like, if out of the blue Luke started flying. Eh eh, I'm not buying it.