The reason I'm barely interested in how prospect pools rank is that they don't even attempt (largely because it's not the goal of the ranking) to account for the strength of the NHL roster at the top of the system. It's one thing to have an ultra strong prospect pool, but if your roster is trash, you actually need a huge majority of those guys to hit in order to turn your organization around.
Let's take Toronto's roster. The following are the current NHL pieces that I would consider to be "core" pieces for the foreseeable future.
C: Auston Matthews
C: John Tavares
LW: Matthew Knies
LW: Bobby McMann
RW: Mitch Marner
RW: William Nylander
RW: Max Domi
D: Morgan Rielly
D: Chris Tanev
D: Oliver Ekman-Larsson
D: Jake McCabe
G: Joseph Woll
If you assume that there are 6 remaining forward spots, 3 remaining defense spots and 1 remaining goalie spot that are not part of the core, you expect free agency to take care of at least 1/3 of those spots, with 2/3 of the remaining spots being filled by the prospect pool. Let's call that 4 forwards, 2 defense and 0 goalies that the prospect pool has to produce of the next few years.
Now let's look at the prospects in the system that I think have a reasonable to good chance of making the NHL in the coming years, and try to project where they might slot into the lineup.
Forwards
LW/RW: Eastan Cowan (Top 6)
RW: Nikita Grebenkin (Middle 6)
C: Fraser Minten (Bottom 6)
C: Alex Steeves (4th line)
LW/C Ryan Tverberg (Bottom 6)
LW/C Jacob Quillan (4th line)
Defense
Ben Danford (Bottom 4)
Topi Niemela (Bottom 4)
Noah Chadwick (Bottom 4)
Cade Webber (3rd pair)
Goalies
Dennis Hildeby (potential starter)
Artur Akhtyamov (potential starter)
Obviously, not all those guys will make it. There will also be 1 or 2 guys that I missed that wind up becoming players, but the reality is that the prospect pool is actually fairly respectable given how few players it needs to produce in the coming years to keep Toronto strong. Yes, you can make the argument that there isn't much projected top 6 talent in the forward pool, nor is there any top pairing defensive talent in the defense pool, but there also aren't many spots to fit those guys. Between Matthews, Marner, Nylander, Domi, Knies and Tavares, the top 6 forward spots look to be mostly filled for the foreseeable future. The same thing goes on defense. Rielly and Tanev are expected to be 1LD and 1RD for the foreseeable future and there looks to adequate current roster talent to fill out the 2nd pair. Therefore, we're really talking about the bottom pair and I' pretty comfortable with those options.
Thanks for this, it is an interesting and relevant way to look at our prospects and what we need from them. I would say that the outlook might even be a bit more positive than you paint.
You mention we will need 6F 3D and 1G and that 1/3 of these may come from FA. One of two of these free agents could be too end guys, say a 2C or a top six winger if Nylander shifts to C successfully. Getting one or two top end pieces (F or D) allows some of cor pieces to "slot down", say Tavares or Tanev, as they get older and reduces the requirement for prospects to quickly fill top and roles.
You left out some tweeners that could play a role also. Holmberg, Robertson, Dewar, Liljegren and Benoit are all young enough to continue to grow into core pieces. If not, their trades my add return that would show up as named players or prospects in this model.
Also, and I know you said you may have missed a name or two. I would add Hirvonen as a bottom six F option, not a sure thing but another iron in the fire.
So what does this look like:
Knies Matthews Domi
XXXXX Nylander Marner
Tavares YYYYY McMann
Dewar ZZZZZ AAAAA
BBBBB
Rielly CCCCC
McCabe Tanev
OEL Liljegren
Benoit
Woll
DDDDD
XXXXX = FA, or Cowan, Grebenkin, Robertson, or Holmberg
YYYYY = Minten, Cowan, Grebenkin, Robertson or Holmberg (JT can be C or LW)
ZZZZZ and AAAAA = Minten, Quillan, Grebenkin, Holmberg, Steeves, Tverberg, or Hirvonen (Dewar can play C or LW)
CCCCC = FA or Niemela, with the rest of our prospects having to win jobs and knock people out
DDDDD = Hildeby or Akhtyamov
We actually may have a lot of competition among prospects for very few openings and this is a great thing. If we end up with a few of these guys making the jump we end up with them as trading chips or pushing other guys to that status.
Our cap space is pretty good too in support of the FA objectives. The cap keeps going up by at least $5M per year and that will cover raises for Knies, McCabe and even Marner. JT coming off a being resigned at a discount is a big save, Kampf and Jarñkrok and possibly Liljegren and Stolarz being replaced by league minimum ELC guys provides a good amount of cap flexibility too.