I'm not really a huge Ochai fan either(he showed his warts in summer league) but I think you underrate the value of him and Sexton.
Maybe Sexton + THT + Simone + 1FRP could get it done? Sexton could be rerouted to a team like Orlando who would send another FRP (Denver '25) + expiring salary(Harris/Anthony) to Portland so they end up with two FRPs. That would be an actual deal I'd consider with Jazz only sending out one 1st.. Not sending 2 FRP's for Jrue at his age and potential expiring contract. *Maybe* send out someone like Sensabaugh instead of Simone if it moved the needle.. Regardless of Jrue, I think Ainge is patiently waiting for a big fish who matches the Lauri/Kessler timeline to eventually come available so it will be important to keep the asset warchest full as possible.
FWIW I met Jrue a handful of times in the early 2010's. I was living in Chatsworth outside LA and Jrue would run his basketball camp at a church down the street. My son was in grade school at the time and Jrue was one of the nicest people you could meet. Patiently took pictures with my son too. Even back then he was saying he would finish his career in LA. After playing on those Milwuakee teams I would guess he would be all about playing for a contender or playing back home in LA.