I believe our two biggest issues are the lack of a secondary ball handler, and an interior presence on defense. We can take care of the ball handler issue with our lottery pick (Goodwin, Carter-Williams, or Smart), but could address the interior defense issues via a couple proposed trades.
The Bucks have a plethora of young defensive minded bigs, but none that you would conceivably throw the ball into and let them go to work. Our issue is almost exactly reversed, with our bigs being more offensive minded. Swapping a couple of these seems beneficial for both teams. So, here is the trade:
Bucks Get: J.J. Hickson
Blazers Get: Ekpe Udoh
There may be some wiggle room for expirings and draft picks being swapped as well, but those two would be the main pieces. My primary concern with Udoh is his rebounding, but according to Hollinger that seems to be a product of his shot-blocking, as he will take himself out of rebounding opportunities in an effort to get to shots. But his defensive stats are great for a young big. He also makes his free throws, which may hint at the fact he could be trusted to hit an elbow jumper or two off of Aldridge kick outs.
The second trade involves the Fakers. If they're truly committed to D'Antoni's system they need to get some players on their roster that actually fit with that style. It just so happens we have two on our roster, Babbitt and Jeffries. So, here is the trade:
Blazers Get: Jordan Hill
Hill is a terror on the offensive glass, and is basically a bigger version of JJ Hickson. He could either play with Aldridge or back him up, and would also pair well with Leonard coming off the bench. Jeffries had the best year of his career last year with D'Antoni, and Babbitt could be the new Steve Novak with Steve Nash dishing him the ball, and Howard masking over some of his defensive deficiencies.
Udoh and Hill are signed through next year, so they do eat up some of our cap space next off season, but they are young and talented, and the type of player that we would use that space on anyway. And you aren't committed to them long-term as you would mostly likely have to do with someone you signed in the off-season.
If you combine them with a good draft pick and a smart FA signing or two, next year begins to look a lot brighter. Maybe something like this: