I have seen many posts proposing taking Drummond at 6 (assuming he is the last of 'tier 2' on the board), then trading 11, Claver and/or Freeland, plus more picks, cash, other filler for 8, where Lillard is our pick.

I have not seen the argument made to pick Lillard at 6, then trade up to take Drummond at 7 or 8. I prefer this strategy for the following reasons:
1. Lillard can get his own shot (and hopefully create for others). A skill not only noticeably lacking in others in this draft, but currently extinct on this Blazers team. I believe this is why Lillard will be valued more than Drummond.
2. Building on the last part of point 1, I doubt that Toronto will deal if Lillard is still on the board (I think they value Lillard as high or higher than we do). However, if Lillard is off the board, our Euros plus Rivers, Waiters, or Lamb, will be more enticing to them to get the deal done.
3. By picking Lillard first (and ensuring we can get someone to create offense), even if Toronto won't deal, and Drummond goes to say Detroit or NO, there are more options of players that have comparable skills to Drummond than if we miss on Lillard (see Leonard, Moultrie, Melo, Zeller, Sims, PJ3).
4. If I have to make a choice between 'he may not make it because he has not done it against elite competition, but he'll kill himself trying' vs. 'if he would focus and dedicate himself, he'll dominate', I'll go with the guy where you don't have to question the effort.
Please, let me know what you think.