Fascinating list.
Like many stats they are an indicator not a definer.
Not to be pedantic, Nathan has coached two finals campaigns (acquired a finals team; as did Chris Scott) and has thus far only missed three finals series (this year would be the fourth, not looking that great so far).
I love exploring the records of flag winning coaches. They are telling.
But one thing I've always noticed, is a few telling signs.
All these coaches look in charge, have authority and obviously have strong football knowledge.
One other thing they all have, is a quality team, often laden with lots of top level talent.
That surely can't be a coincidence.
The premiership coaches that do it multiple times (era sides) tend to have stars and more stars. Not every star is always available but they overall they are there.
But that is just "coincidence."
Clarkson: Franklin, Hodge, Mitchell S, Roughead, Rioli, Burgoyne, Crawford (one flag), Lake etc
Thompson: Ablett, Bartel, Johnson, Scarlett, Kelly, etc
Matthews: Voss, Black, Ackermanis, Brown, Lynch, Leppitsch etc
Jeans: Matthews, Brereton, Platten, Dunstall, Tuck, Buckenara, Jarman, Langford (amazing they didn't win more flags) NB: Joyce also had this list pretty much sans Matthews
Sheedy: Madden, Watson, Daniher, Baker, Weston, etc then had Hird, Lloyd, Mecuri, Misiti, Long etc
In conclusion there is more to coaching than meets the eye.
Nathan may never reach the ultimate success, only one in 18 succeed each year, but it is amazing how the key factor in success (the players, hello, the players!) is sometimes not as well regarded as who is who in the FD or who is who in admin etc. or even who is being the medical guru. Important but the players go and do the business.