Nice question to put up. I give records a couple of spins, and if it doesn't click, drop it and move on. Usually, it is _years_ before I come back to the particular record and give it another try. I find that it comes down to a couple of things:
First, things change over time. Life happens. I'm bringing different baggage when I give a record another shot. In a word, context.
Second, I'm not hearing it the same way I did originally. Different bits of kit in a different environment. In a word, container.
The muso I wind up going though this with on an annoying regular basis is Bob Dylan
