I have to say I think you're talking yourself into some major disappointment at the trade deadline
not necessarily because your analysis of issues is wrong. But because your valuation of Blazer players is off by quite a bit. Simons is a good player, but the very reasons you want him traded are the reasons his value isn't as high as you imagine. A 6'3 guard with non-all-star talent who plays shitty defense and can't be a wing has limited value, and an even more limited market. And a wildly inconsistent, traditional, C who can't play on the perimeter, with a 3-year/18M year contract, and an extensive injury history might not even have positive value
Hart seems to be the most desired asset, but in the last 6 games (and teams are paying attention right now) he's gone 1-15 on three's. Not a good look for a 'shooting' forward
finally add the fact that Portland has no encumbered 1st round picks, and and only one 2nd round pick before 2027 and the Blazers are kind of fucked for making any trajectory altering trades