What Ortiz is doing looks plenty sustainable to me, and now the partial season in the bullpen looks almost like it was the ideal plan all along. He should be in plenty good shape to finish out the season as part of a 6-man rotation. It will be fun to see how well he can maintain this pace.
I'm all for dealing from positions of strength, but prospects are prospects for a reason. Ortiz now has a clear foothold as a young pitcher in MLB. Even if he still has some bumps in the road and is more of a #3-type pitcher, that's insanely valuable at league minimum. Pitching is also about attrition, and you can't take depth for granted too much.
All of that is to say that I would be hard pressed to consider moving Ortiz in a deal. I guess maybe if it were Robert, but that doesn't make a lot of sense and I don't think we'll be in on him regardless.
I also don't think we should just shove Harrington out the door, but in terms of ceiling, I think there might be something to selling high. I'd still be comfortable with him as a main piece in a Chisholm trade. Chandler has more ceiling as a frontline starter, and I see Ashcraft and Harrington as both solid depth that could be called on within the next year or so.
In terms of Jazz, while it's fair to question how impactful the bat would be, I think there's something to just not overthinking it. He can play center just fine and is a top-10 player in wRC+. He adds energy, speed, and legit power, and fills a spot we can't fill otherwise for 2 more years. I also worry that we might underrate how much Rooker will cost. The defense and age will be concerns, but he's still totally raking and would be an immediate huge impact in any lineup. I wouldn't really wince at moving Harrington at the head of a package for Rooker, either... at some level you just figure the defense out.
In any case, we'll see, but if we sweep the Phillies and win the series vs St. Louis, the spotlight will be bright on Cherington. And I am plenty fine being greedy here: the Phillies are sending out a middling young pitcher tomorrow and Gonzales has looked fine. We can finish this sweep, though random middling young pitcher is often kryptonite for us.