I thought of a pretty good test to see if my book reads well. I've posted here before about how you lose your perspective after a while. You can't see your book the way a regular reader sees it. And that's probably a good thing, because if you knew how badly it sucked during the first few drafts, you might not pick it up again.
Anyway, I did think of a way to check how it's working -- do a search & replace and change all the characters' names, then read the book.
This gets rid of a lot of the associations you've had, through living and breathing with these characters for a few years. You're only changing the names, but it's a useful exercise. Of course, all common names have associations with them - at least, depending on your experiences. You have to choose a name that at least SEEMS in line with the character. A nerdy kid doesn't have to be Bubba.
Changing other things might work, too. If you have to listen to certain music for your book to work, stop that. Cut the music and see if it still works. Needing certain music is an early, amateur mistake. (More commonly made with screenplays. Although, as I've said before, if you're Tarantino it's okay. Or Paul Thomas Andersen. Or other guys who I'm not enough of a film buff to know about, who infuse their ouerves with song. [The whole idea of music changing the entire mood or tone of a film could be a topic for another day. Thoughtful music is commonly added to a movie involving a teenager if you don't want it to seem like a 'teen flick' - see The Graduate, Tadpole, etc. Try the scene from the Graduate with Dustin Hoffman driving across the bridge in his car, with Huey Lewis' "Power of Love" on, and see how you feel.])
Where was I?
Well, it's 3 a.m. Do you know where your boss is? Maybe standing over your shoulder. Go back to working on your novel -- I mean, go back to work!!! And be thankful that you're not outside, six stories up.
It all comes full circle here at addledwriter.blogspot.com.