If Harkless were still shooting the three-ball well, I'd agree that he could fetch a protected first-rounder. If his three-point shooting turns out to be a one- to two-month fluke, he's actually slightly overpaid and not really valuable enough for a team to send a first-rounder, in my opinion. I also think you're overvaluing Vonleh. His scoring efficiency is incredibly poor and he's not currently a good defender. His athleticism and age mean he still has some upside, but he's in the NBA long enough that he's no longer a particularly promising prospect. I think he's currently more valuable to Portland as a player than he would be as a trade chip. Portland is at a stage where they can just play him more and think of him like a lottery ticket--low chance of hitting on it, but a potentially large reward. As a trade chip, he'd just be filler, not someone who'd bring back value himself. In my opinion. I agree that Plumlee could likely bring back a mid-first-round pick.
I wonder if the Bulls would be interested in Meyers? Hoiberg's offense is built around the three ball, but his dumb front office gave him Wade and Rondo, two of the worst 3-point shooters. I think Hoiberg would love a player like Leonard. Wonder if we could get Bobby Portis for Meyers.