I tend to agree although I think it's important to realize the Leafs already have some good young players in the system and on the roster - Rielly and Nylander for example. Therefore while the Leafs technically weren't "rebuilding" at that time, those good young players (along with some others in the system) will be able to help the club sooner rather than later.
The key thing will be to hit it big with a prospect in this draft and next (where the Leafs will likely be a bottom 7 team again). A couple more blue chip prospects could help turn this team around and the Leafs could be in the playoff mix in 5 years - not necessarily a cup contender, but a team that's ready to take the next step into one.
Another key aspect is to continue to get as many picks as possible so that they can hopefully get a gem out of the rough. Tampa Bay, for example, would be a team to model this after.
I think we'll know when this rebuild is over when we see a couple of quality seasons in a row that see the Leafs in the playoffs, being primarily led by some of the young players on the team who are taking their game to the next level.
There is definitely the technicalities that go along with building o et the long haul that can be advantageous in various ways with regards to timeframe to build. Blind luck included. The process has to include build extreme depth and a determined path of development that is never rushed. Cap space availability has to be implemented into every season I believe in order to reap a advantageous position with regard to options at deadlines.
Every possible advantage is going to be available with patience,development, and most importantly a dedicated identity of the way the team is going to play,excluding rule changes in the league. There is need to decide style of play and I believe there is definitely a need to draft with a eye on insulating skill players with toughness beside them. Big wingers with skill,speed,determination and net presence.
The Rangers have two defensemen in the top fifty in scoring for example. Yandle just got there by trade but there own guy sits at 45 in scoring by defensemen. They got Yandle because they decided they needed a power play quarterback. Rightfully so. They were very successful without it though and they are taking their run this year. That's the technical stuff that is mostly unforeseen.
You have to have cap space options for them reasons. Its so technical that its to much for one post.
Team style of play,draft,development and manage the cap properly is a great foundation I believe.