I honestly think 5 years is a long ways to project, if we don't make the playoffs or contend for the next 5 years then Tim Murray is likely gone as general manager.
In this day and age with so many teams against the cap it should be relatively easy to acquire NHL talent opposed to the past. Look at guys like Boychuk and Leddy being moved for a couple picks and a decent prospect, I look at a guy like Loui Erikkson as a guy that could be moved because of salary cap implications with the Smith, Krug and Hamilton extensions on the way. This is just one example but we are primed perfectly to get good players off teams that need the cap space.
Obviously a big part of the speed of this rebuild is going to be whether or not Ristolainen and Zadorov can be legit top 4 D-man sooner then later, the way they have played indicates they might be there by the end of the season if not sooner, especially in Ristolainen's case.
How good are Sam Reinhart, Joel Armia, and McEichel going to be next year?
Goaltending...Enroth is not going to be the anwser, and no one from the AHL is ready yet, Neuvirth has played pretty well but I don't know that he is the answer either.
In summary, there are far to many ????????? to say 5 years is best case scenario, in 5 years Reinhart and McEichel will be 24 and 23, Toews and Kane won a cup at 20 and 21, Crosby and Malkin won a cup at 21 and 22 years old, Ovechkin made the playoffs in his third season with 19 year old Backstrom as the teams #1 C . Not saying we are following that path, but if you can get a good core of 4-5 guys to surround Reinhart and McEichel the playoffs could very well come before 2020.