The issue with Waiters for me is that he's very redundant of Irving's skillset. Neither one is a very good passer, and both are best as scorers when they have the freedom to penetrate, and neither one is particularly good operating off the ball.
This kind of setup worked well for OKC, but in a Lebron-less league, and on separate teams, both Westbrook and Durant would be MVP candidates. Irving should get to that level if he can stay healthy for 75 games or more, but Waiters isn't that guy. Luke Walton played major minutes this year for Cleveland because he actually made up as a facilitator when Irving or Waiters (or both) were on the floor.
They could work together, but they need a 3 who spaces the floor, passes well, and defends. I think they'd be just as well off trading Waiters for a 3 and D 2, and looking for a facilitating 3.
Gordon Hayward would be pretty awesome there.