The first thing I do when I buy a tune book is go through it and (try) to play all of them cold. Then, I give it a rating, 1-5. If a tune really grabs me the first time I play it, I learn it right then. Later, if I am bored with the cheat sheet, I go back and find one I liked earlier.
Problem is the BIG tune books. I've owned the Fake Book and Coles for 10 yrs and still haven't gotten all the way through!
I have never had a problem like Astorsen; I play obscure tunes in sessions and they always seem to be well recieved. Sometimes others learn them, sometimes not.