That’s one way of doing it but you are kicking the can down the road 3 years and even then you are probably just a playoff team. Considering their loyalty to Dame the more likely scenerio would be for them to trade Sharpe and picks for a star. Dame is 32 and if he ages like Steph he has 3-5 more years of prime left. If Evan Mobley can get consideration for defensive player of the year in his second season imagine what the best prospect since Lebron can do. If you trade Sharpe for a second star and can build around those 3 plus Simons you have a real title shot. If it doesn’t work out you have Dame and the second star to sell off for picks and rebuild around Wemby.
The Blazers are hitting a tipping point. Lillard will turn 33 this offseason.
If they want to hold on to him and give him a chance to compete, they don't have a lot of options. Sharpe by himself isn't returning a 2nd star. He showed flashers to end the season, but would Toronto give up OG or Siakam for him? Would Washington trade Beal for him? I don't see it.
Sharpe plus 2 or 3 future 1sts? Maybe. So if the Blazers win the lottery and land Wemby, would it make sense to mortgage future assets to make a push with Dame for the next 2-3 years and be short FRPs when he leaves or retires and you have to build around Wembanyama?
The other part of it is that if Portland were fortunate enough to land the #1 pick, I think you give that kid as much freedom as possible his first year. Don't put playoff pressure and Dame's legacy on him. Let him make mistakes, try things he may not be ready to do yet and test his limits vs being in a Keegan Murray like role where you minimize what you do on both ends to limit mistakes and focus on immediate wins.
Do you mortgage the future to try and win now with Dame? Or do you sacrifice the present for draft capital and cap room to build around young talent?
Because the middle road of standing pat with an aging Lillard, a handful of vets like Nurkic, Grant, Winslow and trying to win games while also developing your young players is likely to end with the team doing neither.