I mean no disrespect, but equating the offensive impact of Simons or Pritchard to a healthy Lillard is just misguided. The obvious huge "IF" applies, but IF Lillard returns at a healthy All-Star form, he's an offensive weapon of a caliber that the other two just are not. Lillard is a guy who can score against strong playoff-caliber defense. You tired of iso Tatum at the end of quarters? Lillard gives you another option. Meanwhile Pritchard struggles against those strong defenses (he beats the pants off the Utahs of the league though) and Simons just spent two years trying to be the guy with poor results.
Yes, of course it's possible - even likely - that Lillard isn't that guy anymore. That's the risk. That's why there's a chance we can afford him at all. But we're not in a position to be picky. We're capped out, our assets are spent, our young prospects have "average roleplayer" ceilings, and our star is in a boot. If you honestly want to take another shot at contention with this core, IMO you take a chance on Lillard. Otherwise you sell off and rebuild.