Cradle by Will Wight is the king of endlessly re-read-able series, IMO. A young man in a world of magical martial arts sets out on a quest to save his home from foretold destruction, and overcome an initial disability to become one of the strongest people in the world (necessary to save his home when the time comes).

Hard to explain what's so incredibly compelling about this series, but if you like fantasy (particularly progression fantasy or cultivation stories aka xianxia) I urge you to give it a try; I highly doubt you will regret it. More re-read-able than Harry Potter, and without the casual misogyny (in a world of magical martial arts, women are just as capable, and dangerous, as men are) or obnoxious the-awful-status-quo-is-okay bullshit (but explaining this in any more detail would probably involve spoilers, so I won't).

Is it high art? No, it's fairly schlocky, but it's really fun to read, in a way that many other series fail to be, even really good ones like Red Rising or Stormlight. And while it doesn't end all wrapped up neatly in a perfect bow like, say, Mistborn (the trilogy, not the sequel series), it doesn't exactly fail to bring plotlines to satisfying conclusions.