There's very possibly something I'm missing and that is horrible about him, but what is the feeling on Anfernee Simons? Portland looks set to go all-in on Sharpe and Scoot, and probably will look for a quick rebuild once they trade Lillard.
His contract is great, so the cost might be steep, but you could then turn around this summer or next and turn Jaylen into a couple roleplaying wings/bigs + replenish picks, while still having a ton of playmaking/scoring talent between Tatum, KP, Simons, and DWhite. You probably would have to split him and White up against some opponents and make one a 6th man, but whatever.
I'm just really into the idea of turning Jaylen's salary slot into a scoring guard and 1-2 secondary wings, so I'll probably keep barking up the tree of every reasonable guard until something happens. Garland is the other one in that mold whom I'm into.
When you have a few shot blockers, and a lot of other good perimeter defenders, I'm just not that worried about finding ways to make it work with 6-2 type guards who are true scorers.