Here's my take on it:
Organizational
Shanahan hasn't done anything in the game of hockey at a management level. As a fan, I can get behind him because I recognized what he did as a player and his level of accomplishments on the ice. As an executive, it is way to early to say that he's a good or bad addition.
I think the Leafs as an organization is run fairly poorly. As a business, they have done very well. As an organization, they continue to raise prices with a poor product. It's like a toy company making an awful toy that continues to have manufacturer recalls and yet people are so enamored by it, that they just have to look past it. I don't want to get too far into it right now but the basics of it would be that Leaf fans reward failure.
Team Management
I don't like the mentality that people have with Nonis is just a temporary GM or anything along those lines. It's obvious that he was qualified for the job or else they wouldn't have gave it to him. He has made some terrible decisions and he's also made some smart ones as well.
Development/Marlies
The Leafs have done an AWFUL job with bringing their players through the system. I can't believe how bad they've been with this aspect.
It wouldn't matter if you had Scottie Bowman in his prime coaching the Marlies every season. If they don't have a place to go when they've developed at that level, then what's the point. The last player that actually played a full season with the Marlies before playing with the Leafs was John Mitchell... who was a 5th round draft pick from 2003. Take a look at their draft history and look at the players:
Kadri - was back and forth for parts of 3 seasons
Rielly & Schenn - both started with the Leafs
Frattin - came right out of college and then got sent back
Kulemin - started with the Leafs from Russia
Reimer - you could make a case for him, but he was back and forth from the AHL to ECHL a lot and never carried the load of a full AHL season
Stralman - started with the Leafs in his rookie season and got sent back down
If you think about that, over the past 10 years, there has been only 1 player that was fully developed and ready to play for the Maple Leafs in a full time role. I'm not talking about guys that come up and play 20 games and get sent back down.
And I will go back to my favourite team in terms of development within that same time frame, the Detroit Red Wings. They've managed to develop players including: Jimmy Howard, Kyle Quincey, Jakub Kindl, Justin Abdelkader, Darren Helm, Brendan Smith, Joakim Andersson, Gustav Nyqvist, Tomas Tatar & Tomas Jurco.
If that doesn't blow your mind, I don't know what will.
Ohh and I should point out that they haven't missed the playoffs basically since a majority of people on here have been alive. haha
Scouting
Recently, it seems like the scouting staff has woken up a bit. Because I don't even want to get into how bad it was in the early 2000's.
I'm on the fence with trading picks though. I don't care if you trade a 7th rounder or a 4th to get a solid veteran. But when you trade 2nd round picks for Holland, Bolland and Bernier, sometimes it doesn't work out.