A week ago we talked about a New York Daily News report that mentioned the Raptors as possible suitors for Jeremy Lin, by way of a potential back-loaded contract.

Already this week, the New York Post writes that “a source confirmed” Toronto will be an offer sheet suitor for Lin and ESPN.com has Toronto No. 1 on a list of teams besides the Knicks that might go after the young point guard.

One thing that hasn’t been given much thought yet though, is whether Lin would be a good fit in Toronto and whether signing him long term would be a good decision.

To really get a grasp on an answer to those questions, we have to look at what the options are at the point guard position for the Raptors next season, and going forward.

The obvious option is to keep Jose Calderon around for the last year of his contract (at around $10.5 million). Calderon has proven to be an underrated and probably an under appreciated starting point guard who can make teammates better offensively, but who is still a liability defensively, despite some improvements in that area of his game this past season.

I get the feeling that Calderon is one of those guys you kind of take for granted while he’s here, and then realize he’s hard to replace once he’s gone. Nevertheless, he’ll be 31-years-old when the 2012-2013 season begins, and his durability has always been an issue. Calderon has only played a full 82 games once in his seven-year career, and has missed 13-18 games in a season five times already.

Jose can probably evolve into a solid veteran point guard off of the bench for a contending team in the next season or so, and if it happens in Toronto, that’s great. But realistically, it’s hard to see him keeping the starting job with the Raptors much longer.

Jerryd Bayless is a gritty young point guard who has yet to be given a full time starting opportunity in the NBA. When he has started in stretches for the Raptors, he’s looked absolutely lights out and actually plays a similar style (penetrating, driving to the basket, putting his body on the line to score and get to the line) to a guy like Jeremy Lin.

Bayless enjoyed his best offensive season in the NBA this past year, and finished with an above average Player Efficiency Rating of 17.7. But like Calderon, his durability is far from a safe bet. Jerryd is tough, but his somewhat reckless style of play could also be damaging to his body and long term sustainability. He’s missed 54 games over the last three seasons, including 35 of 66 games with various injuries this season.

If given the opportunity, Bayless (who is actually just three days older than Lin) might have just as high a ceiling as Jeremy Lin, but based on his issues staying healthy early in his career, I hope the Raptors can keep him around on his approximately $4.1 million qualifying offer for next season. If he stays healthy and earns a long-term extension after that (which I obviously hope he does), all the power to him.

Like Bayless, Lin provides some high risk, high reward potential. The 23-year-old burst on to the scene this season with one of the best starts to a “starter’s career” in NBA history, literally rescuing a team’s season in the biggest and most demanding market in the NBA. However, he was also shut down for the season with a meniscus tear and only played four more games than Bayless did in the lockout-shortened 2011-2012 campaign. In just two years in the NBA, the undrafted Lin hasn’t played more than 35 games in a season yet.

But there is one area where Lin’s presence cannot be doubted.

Outside of Lin looking like a more complete basketball player than Bayless this season, he also has astonishing marketing potential and can be a legit international superstar if he continues to perform on the court. In a multicultural hotbed like Toronto, that cannot be understated from a business perspective. While it would take a risky gamble to acquire Lin, it could pay massive dividends both on and off the court for the Raptors.

I doubt Jeremy can put up the inflated numbers he posted in that Linsane stretch last season, but I do think he can be an above average NBA point guard for the foreseeable future.

As for Nash, I got pretty deep into why acquiring him (at the right price) can never be a bad move a couple of weeks ago, so I won’t give you that spiel again.

The way it breaks down is this. If you want to play it safe, you keep Calderon around and either hope Bayless emerges as a potential star at the point or perhaps you draft a point guard that you think has that capability. It wouldn’t be the worst thing in the world for a young point guard to learn from a guy like Jose Calderon.

If you want to see what Calderon can fetch you as an expiring contract on the market, then maybe you trade Jose and give Bayless an opportunity to prove himself as a full time starter for the year.

If you’re up for a gamble, and think this team can be pretty good as early as next season, then jumping into the bidding for the likes of Steve Nash or Jeremy Lin is for you. Nash is a bonafide Hall of Famer, one of the greatest point guards of all time, a proud Canadian, and despite his age, has proven to still be one of the more reliable point men in the Association. If the Raptors can nab him, it’s hard to see the fault in that acquisition.

If the Knicks land Nash, then prying Lin out of New York should become a little easier (if Nash signs elsewhere, you’d have to assume the Knicks do whatever it takes to retain Lin).

Lin is an exciting young player with team-leading potential who could be a marketing and business bonanza. If he’s a hit, you strike gold both on and off the court. If he’s a miss, you probably end up with a very bad contract on your hands that isn’t exactly easy to get rid of.

On one hand, you could say that attempting to build a championship caliber team in Toronto requires near perfection from a management perspective, and therefore that taking risks is too big a gamble. On the other hand, you could say that the only way to break into the NBA’s elite class of organizations while running the Raptors is to take big risks and hope you hit a few home runs along the way.

Which side of that spectrum Bryan Colangelo and company are on will go a long way in dictating how the Raptors establish themselves at the point guard position this off-season.