The thing is, I'm fine with the Boogie plan failing. If 2 years from now, he doesn't pan out you trade him during his final year for picks. You hardcore tank the next year, get a #1 pick, and hopefully whatever you kept keeps developing. You can use your top 3 pick in a package for whatever allstar is on the market then, and give free agency another go. If you don't trade him you have a great young piece who should be on a higher level than CJ, Meyers and Vonleh are now. You then use cap space for young guys or lopsided trades.
Also, if we get Boogie, we'd just need him to not go downhill and we'd be in good shape. I think he'd be fine in a better culture and organization. And we wouldn't need to add a star free agent. We could surround him with solid vets whow fit well, like we had last year, but we'd also have enough cap to build a top 10 bench. Then the cap goes up from around $90M to $10M, and depending on the extensions of big men we have, we could have $10M in cap to add to that group, or at the very least, our MLE and Bi-Annual Exceptions.
Keeping on this track likely puts us in the place no one wants to be down the road.... a fringe playoff team. It's hard to get out because either you get lucky or, most likely, you get bad again to try to reload again. Thing is this reload would be further down the road, and we might not have enough time left in Lillard's prime for that.