When it comes to making important decisions on upcoming restricted and unrestricted free agents, teams have a number of factors to weigh when deciding whether to begin negotiating a top-dollar deal, make a trade or slow-play the situation.
Organizations will ask themselves: What is their timeline to compete? Is the player's current performance what can be expected over a period of time? What salary-cap implications will a new contract have?
As we approach the dog days of the NHL season, let's have an early look at some of the most interesting UFA and RFA situations for the upcoming offseason and the best approach for each player's team going forward: new contract, trade, or wait and see.
2019-20 unrestricted free agents

Jeff Skinner, LW, Buffalo Sabres
Key stats: Outscoring opponents 20-11, with 53.1 Corsi for percentage while skating with Jack Eichel
Sabres' best option: Sign Skinner to an eight-year contract
Skinner has been an impressive offensive player in the NHL since day one, clearing 20 goals six times and notching 30-plus goals three times in his eight seasons with the Hurricanes. In Buffalo, the 26-year-old winger has been on fire, tied with Boston forward David Pastrnak for second in the NHL in goals with 19, and playing a major role in pushing the Sabres to the top of the NHL standings.
The major concern with signing Skinner to a massive contract now is that he's shooting a whopping 23.2 percent after scoring on 11.2 percent of his shots over the previous eight seasons. Normally that would be a sign that the club should wait to see if he continues to produce, but combining Skinner's past production with his outrageous chemistry with young superstar Eichel, it makes sense to lock him up as soon as possible and solidify a top-notch top line for a very long time.
Salary cap should not be a big concern, considering the Sabres will see some contracts come off the books after 2020 and only have three players locked up past 2021.

Matt Duchene, C, Ottawa Senators
Key stat: 1.27 points per game, a career high
Senators' best option: Trade Duchene as soon as possible
Duchene has always had quality scoring and shot-differential numbers, but he is off to a blazing-hot start this season. The former Avalanche star has produced 33 points in 26 games on the back of a career-high 15.5 on-ice shooting percentage. With regression likely, the Sens should put Duchene out on the market as the standings start to shake out and teams get desperate to find a difference-making player. If Ottawa waits around, Duchene's production -- and value -- could slip.
Of course, they have the option of trying to sign him to a long-term deal now, but it's hard to find any reason for Duchene to sign early to stick with a rebuilding franchise rather than becoming the most sought after scorer on the market next offseason. And since the Sens are an incredible long shot to win the Stanley Cup this season -- to put it charitably -- there's no reason to hang onto an upcoming free agent with big trade value.
Ottawa could wait until the trade deadline, but that approach can be risky (as they found out with Erik Karlsson). If other scorers are on the market, the Sens could end up with far less than expected in return for their center. This decision will have an oversized impact on the next few years for this franchise.

Artemi Panarin, LW, Columbus Blue Jackets
Key stat: 3.27 even-strength points per 60 minutes, 15th in the NHL
Blue Jackets' best option: Wait until the deadline to make a decision
Signing Panarin to a long-term deal won't be easy considering the Blue Jackets' salary-cap situation. They have $31 million in salary already locked into forwards through 2021. The Jackets will also have to sign former top picks Zach Werenski and Pierre-Luc Dubois within the next two offseasons.
Panarin is worth the price. He has been remarkably consistent over his first three NHL seasons, producing 77, 74 and 82 points. The 27-year-old winger is rolling again this season, with 27 points in 24 games.
If Columbus knows it cannot sign him to a long-term contract -- and he has dropped many a hint that he wants to sign elsewhere -- the best option is to wait and see, considering they are in second place in the Metropolitan Division and have a team stacked with scoring forwards, dynamic defensemen and a Vezina Trophy-winning goalie in Sergei Bobrovsky (also a pending UFA). If the Jackets stumble and fall out of contention before the deadline, they will have a pair of highly valuable trade assets. If they're still in contention, Stanley Cup banners hang forever, so it might be worth hanging on to the dynamic scorer and elite netminder.

Erik Karlsson, D, San Jose Sharks
Key stat: 59.6 Corsi for percentage, third best in the NHL among defensemen
Sharks' best option: Sign Karlsson to an eight-year deal (after the trade deadline)
Karlsson has shaken off a slow start, with eight points in his past seven games. We can probably expect more goal scoring to be on the way as the Swedish superstar has only found the back of the net on 2.7 percent of shots (he has a 6.8 percent career shooting percentage). The other indicator that Karlsson has worked out well thus far as a Shark is the team's shot differential with him on the ice: San Jose has outshot opponents 280 to 213 at even strength, which is on par with Karlsson's puck dominance historically.
With the Sharks in a situation in which they have long-time core players in their mid-to-late 30s, they need to find players to build around in order to remain in contention. They signed Evander Kane to a long-term deal this past summer to lock up a scorer, now they must find a way to keep Karlsson to lock in a top-notch defense corps for years to come. Otherwise, he will have been a very expensive rental.

Wayne Simmonds, RW, Philadelphia Flyers
Key stat: Lowest points per game since joining Flyers, despite 15.8 percent shooting percentage
Flyers' best option: Trade Simmonds at the deadline
Simmonds has cleared 20 goals in six straight non-lockout seasons, and notched 30-plus goals in 2015-16 and 2016-17. But at 30 years old, it's tough to project whether he will continue to score at a high level, and the veteran winger isn't the type of all-around player who will drive possession or shut down opponents on defense. While plus-minus can be a severely flawed stat, Simmonds is going on nine straight seasons as a minus player, and nine of 11 seasons of posting a negative shot-attempt differential.
The Flyers would be wise to build around their two young defensemen, Shayne Gostisbehere and Ivan Provorov, along with 2017 No. 2 overall pick Nolan Patrick. They don't appear to be in a position to win now and would be best served continuing to build through the draft and finding short-term options on the free-agent market to build the roster next season. The recent firing of GM Ron Hextall may alter the strategy somewhat; however, Simmonds could be a player they use as part of a larger trade package.
2019-20 restricted free agents

Mitch Marner, C, Toronto Maple Leafs
Key stat: 19:24 time on ice per game, career high
Maple Leafs' best option: Play hardball for a bridge deal
Toronto finds itself in a tricky situation with William Nylander already holding out and both Marner and franchise player Auston Matthews set to be RFAs next summer. There's no question Matthews will be getting top dollar, likely in the range of massive contracts given out to Connor McDavid and Jack Eichel recently. Marner is a more complicated case since Toronto already has $11 million per year poured into John Tavares. No team wants to find itself in a Chicago Blackhawks-esque situation in which it cannot afford anyone aside from its top forwards, but Marner scored 69 points last season and is producing more than a point per game this season.
The question is how much of Marner's production this season is being driven by Tavares, who notably helped players like Josh Bailey and Anders Lee become elite scorers. Do the Leafs want to go all-in on a long-term megadeal like that of Leon Draisaitl, with an $8.5 million annual cap hit, for a very good player whose numbers are bumped up by a top-10 player?
If Toronto could keep Marner on a short-term deal closer to Nikolaj Ehlers' $6 million annual cap hit, the Leafs would be in an excellent spot with star players in place and enough cap room to fill out the roster.

Brayden Point, C, Tampa Bay Lightning
Key stats: Career-high 1.27 points per game, 26.1 percent shooting percentage
Lightning's best option: Sign to a bridge deal
The Lightning have made a science of finding undersized players who can straight up score points. Point had 32 goals last season and has carried over his success this season, with an incredible 18 goals in 26 games. It appears Point will be a high-percentage shooter throughout his career, as he cleared 14 percent in his first two seasons, but he's not going to continue his current 26.1 percent mark. Signing Point to a big contract now would be an overreaction to an incredible start.
Tampa Bay will be in a difficult position in terms of the salary cap with more than $51 million locked in to forwards and defensemen through 2023. If Point scores 40 goals this season, it will be a challenge to pay him what he's worth without a serious domino effect. Ultimately, players like Alex Killorn and Tyler Johnson might have to be moved.

William Karlsson, C, Vegas Golden Knights
Key stat: 8.6 percent even-strength shooting percentage, down from 20.3 percent last season
Golden Knights' best option: Wait and see
Last season, the Golden Knights were the darlings of the NHL, reaching the Stanley Cup final in the franchise's first season. A major part of their success was out-of-nowhere top center William Karlsson, who notched 43 goals after having a previous career high of six goals. Not coincidentally, he also had the highest shooting percentage in the NHL.
Karlsson has still produced some points this season, notching eight goals and 12 assists in 27 games, but is nowhere near his 2017-18 pace. Unsure of what they had in Karlsson last offseason, Vegas signed him to a one-year deal. The Knights should not broach the idea of a long-term deal until they have a proper sample size to project Karlsson's future.

Zach Werenski, D, Columbus Blue Jackets
Key stat: Plus-3.8 percent relative Corsi since entering the NHL
Blue Jackets' best option: Sign to big-money, long-term deal
Werenski is more than three years away from being able to rent a car for the best rate, but he has already established himself as a star defenseman who shows no signs of falling off. The eighth overall pick in 2015 has posted double-digit-goal seasons in his first two campaigns, and is on pace for around 50 points in 2018-19. While his shot differentials haven't yet evened out to their normal levels, the bigger sample size shows Werenski dominating the puck and driving the offensive success of his team. Signing him to a long-term deal now -- buying out some restricted years at a discount -- will pay dividends down the road as the cap continues to rise.

Sam Bennett, LW, Calgary Flames
Key stat: 13:27 time on ice per game, lowest of career
Flames' best option: Find Bennett a new home
With just eight points in 25 games for Bennett and a role that isn't reflective at all of a fourth overall pick, it's time for the Flames to see if they can improve the current roster rather than continuing to wait around for Bennett to fulfill his potential. The Flames are sitting in first place in the Pacific Division on the back of several young scorers like Sean Monahan and Matthew Tkachuk, so it's best to get someone who can contribute more now, then continue to keep their fingers crossed on Bennett.
If there was any sign of life from Bennett, then it would be smart for the Flames to slow-play this and sign him to a cheap bridge deal in the summer. But he has now reached 266 games played in his career, with fewer than 100 points. Teams that do not have much chance to compete this season should be interested in taking a flier to see if they can get him back on track.