Big issue 1: Does anyone get fired? GM Neil Olshey agreed to a contract extension that will keep him around until 2021, though owner Paul Allen has enough in the bank to cover Olshey's deal if he decides to make a change.
There have been light rumblings suggesting coach Terry Stotts could be fired, but that would only happen if Olshey goes, too. Allen has not shown much inclination to getting rid of Olshey, so it's likely that the brain trust stays in place.
Big issue 2: What to do about the guards? If the Trail Blazers wanted to make a major overhaul, the only way to do so would be to trade away one of the backcourt duo of Damian Lillard or CJ McCollum. Each would fetch a good return that would allow Portland to add some depth of talent at other positions. But again, that's not going to happen this year with Olshey at the helm, and Olshey is probably sticking around.
The expectation is that the Blazers will attempt to do what Stotts' former Mavericks colleague Dwane Casey did in Toronto this year. Casey altered the team's offense to reduce the reliance on getting the two guards into the pick-and-roll (Portland got more offense from the PNR than any other team this year, as Toronto did last year), and the Raptors were a better team for it.
The Raptors, though, had the pieces in place to construct the best bench in the league, a key to their success this year. Portland doesn't have the same depth, which will continue to be an issue.
Free-agent outlook: The big question is the future of Jusuf Nurkic, a restricted free agent who has helped stabilize the Portland defense even as he has been inconsistent offensively. Nurkic was excellent after the All-Star break, averaging 15.0 points on 56.3 percent shooting, with 10.6 rebounds.
If Nurkic gets a $15-18 million per year offer elsewhere, there's no way the Blazers can match - that vaults them deep into luxury tax territory and costs them exponentially more than the value of the deal. Moreover, the league is littered with teams crying buyer's remorse over big contracts for centers. Portland may decide that it can only let Nurkic walk and hope that Zach Collins is its big man of the future.
Beyond Nurkic, the team will have decisions to make on Ed Davis, a valuable locker-room veteran who would have to take a pay cut to stick around, as well as Shabazz Napier, who had the best of his four NBA seasons last year. Pat Connaughton's contract is also up.
The young folks: If Portland is going to thrive on change from within, Collins is the big hope. He showed flashes of becoming a reliable inside-outside combo big man, and though his numbers were unimpressive (4.4 points, 39.8 percent shooting, 31.0 percent 3-point shooting), he is only 20 and has plenty of development ahead. The Trail Blazers may not be able to wait for that development, though, when they have two star guards ready to win now.
Summer League and G-League star Caleb Swanigan should be ready for increased minutes next year, even if his height (6-8) and, shall we say, voluptuous body type have some wondering whether he can be a contributor. The team took fliers on former first-rounders Wade Baldwin and Georgios Papagiannis, too, and will hope for some level of return from either.
Portland will have the No. 24 pick in this year's draft, and it does not owe future first-rounders to other teams.
Wait till next year: The Blazers won 49 games and plucked the No. 3 seed in the West. Given the recent contract misses by Olshey - there are still two years and $36 million left for Evan Turner, and two years, $22 million for Meyers Leonard - there's no hope for personnel improvement and, in fact, the Blazers may have to take a step backward by losing Nurkic.
Trading either Lillard or McCollum would certainly shake things up, but it's a good bet that they'll give this group at least another year.
Again, the hope is that Stotts can go back to the drawing board and alter the Portland offense the way that Toronto altered its offense. But that's likely wishful thinking. The Raptors have better and more cohesive talent around its star guards, and when you look at the Blazers roster, there are no obvious players for whom you'd like to get extra shots.
It's hard to imagine the Trail Blazers reaching 49 wins again next year, though they should be a playoff team and perhaps could get to the second round with a better matchup.