Most notably is superstar Kevin Love's future. There's little to no chance Love will opt in for his extra year, so the T-Wolves will have to either find a trade partner or let him walk and get nothing in return, the worst of choices for Minnesota.
The result of Love's situation will shape the rest of the free-agency period for the Wolves as they'll try to fill out their roster with pieces that could get them back in the playoffs.
Their second unit is in dire need of shooting after very bad years from J.J. Barea and Alexey Shved. Rookie guard Zach LaVine and second-round pick Glenn Robinson III could both remedy that situation, but they could take a while to pan out.
Minnesota could also fortify its frontcourt with some strength and athleticism as Dante Cunningham is a free agent, and their backups at the 4 aren't very effective.
The Wolves have limited cap space, but some creativity could land them solid rotation players.
Sign a Backup Point Guard
Barea had a very disappointing year, shooting 31 percent from downtown, his second-worst career mark. If his struggles continue, he could certainly find himself riding the pine.
LaVine could fill in as a backup point, but his inexperience might delay his insertion into the regular rotation during the opening weeks. The T-Wolves can always sign a new backup, and there are a few good players available with different skill sets.
Ramon Sessions could be a cheap option.
Sessions excels at attacking and finishing around the basket, scoring on 56 percent of his attempts near the rim. He has had some struggles with his shot over the past few years, though.
If the Wolves want more of a shooting specialist, they can look at someone like Mo Williams.
Williams opted out of his contract with the Portland Trail Blazers recently, wanting a three-year deal, per James Herbert of CBS Sports. If Portland is unwilling to offer him that deal, Minnesota, which needs shooters, could step in and give him a chance.
He has proved to be a streaky scorer throughout his career, helping spark the second unit. He can also play the 2-guard and line up alongside Ricky Rubio, an excellent drive-and-kick player. Williams would also be a solid veteran presence.
Whichever way Minnesota goes, an upgrade is necessary, as Barea may be entering the downside of his career.
Sign a Backup Power Forward
Minnesota needs a backup 4 not only due to the imminent Love departure , but also because Luc Richard Mbah a Moute isn't exactly a great option.
Mbah a Moute didn't see the court a lot, and he hasn't shown much throughout his career and struggles because of his size. He might be more fit as a 3, but the Wolves are stacked at that position.
Minnesota could use some rebounding specialists, and there are a couple of solid options.
First is Jordan Hill, a high-energy rebounder who is also fairly effective from short-to-mid range. He'd be a nice upgrade at power forward as his season averages of 9.7 points and 7.4 rebounds per game are better than Cunningham's and Mbah a Moute’s combined.
The Timberwolves could also look at Jeff Adrien, another rebounding forward who can knock down the mid-range jump shot on occasion. Adrien benefited from being traded to the Milwaukee Bucks, where he found a spot in the rotation and averaged over 10 points and nearly eight rebounds per game.
Even if Love isn't dealt before the season, the Timberwolves would benefit from adding a stronger option behind him, preferably someone who could continue to crash the boards as well as protect the rim.
Trade Kevin Love
Minnesota has to try to get something in return for the star forward. The longer it waits, the lower the value of any returning assets since teams will know they can sign him outright during free agency.
The Golden State Warriors' deal including budding star Klay Thompson appears to have stalled as ESPN.com's Ramona Shelburne and Marc Stein reported. And while that deal made the most sense for Minnesota, as it could build around Thompson for the future, there are still a couple of other options.
The Chicago Bulls apparently have interest and were rumored to have offered forward Taj Gibson, second-year guard Tony Snell along with the two picks they held in the draft, per ESPN's Chad Ford (subscription required).
With the draft now behind us, though, the Bulls could offer a similar package that includes their draft pick along with the rights to Euro star Nikola Mirotic. Convincing Chicago to part ways with so many pieces would be the hard part.
Another option is the Houston Rockets.
They're interested in both Carmelo Anthony and LeBron James, and they will surely clear cap space to make either signing a possibility. Bleacher Report's own Ric Bucher has more on the Rockets as a possible trade partner:
As Bucher stated, a deal is more than likely contingent on the Rockets landing either Anthony or LeBron, as they could then deal Chandler Parsons without a problem. If Parsons is in fact No. 2 on Minnesota's list, it should try to get the deal done regardless of what Anthony or James do in free agency.
Minnesota would add a player it likes and wants and could build around as it looks toward the future and past the Kevin Love era.
Whatever team the Timberwolves choose to strike a deal with, it's imperative they do it fast before teams are unwilling to trade for him and simply steal him during free agency.
It could be another rough season in Minnesota, but adding a few good bench pieces and retooling the roster will at least turn a new chapter for the struggling franchise.
Chances are it will lose its biggest start since Kevin Garnett, but with a new head coach and perhaps a new roster, the T-Wolves could be looking at a postseason appearance in the near future.
Note: Stats courtesy of Basketball-Reference.com.