Lillard didn't seem very enthused in that recent interview.
Essentially, if he is as loyal as he says, I really think this team needs a re-tool asap while Lillard's still got some juice left. If nothing is accomplished now, Neil is really setting himself up for another situation that will bite this team a few years from now. By then, it'll be too late to put anyone next to Dame as he'll be too old (and because, no shit, it's rare to find another 25+ PPG talent who can shoot as well).
Imo, the solution should be to tank for a year or two. I see Mavs, Suns, Lakers, Nuggets getting better while teams like the Hornets, Pistons, Kings, Nets stay in that same mediocre zone that Portland might find itself in come springtime. Essentially, many lottery bound teams have stayed the same or gotten better this off-season that losing Aminu and Harkless (for late first rounders) and playing within the ultra competitive West would ensure the Blazers get a decent lottery pick within the #4-8 range (the NBA just increased lottery odds for everyone outside Top 3 starting in 2019).
Even if the Blazers aren't in place to select a high quality player, having a good pick in the #4-8 range, late first rounders/2nd rounders, and expiring contracts ala Leonard/Turner (along with young talent like Simons or Collins) may be able to net a Jimmy Butler or someone similar down the road. If not, the Blazers will still have cap space in 2020 to sign roleplayers or decent starters to get back to where it is right now.
The solution should be to acquire assets before 2020 rather than wait until 2020 for "more of the same".