I notice a common numerator in three of them.

Regression analysis on the final 162-game regular season shows there was a small positive correlation (+0.20) relative to how early a team was selected within the respective league. But this correlation is basically due to the top 4 picks. If you took an average win total of each group of 4 picks, you get the following...

Picks 1-4: Avg wins 86.6
Picks 5-8: Avg wins 82.0
Picks 9-12: Avg wins 79.7
Picks 13-16: Avg wins 78.8
Picks 17-20: Avg wins 81.9
Picks 21-24: Avg wins 77.1

In aggregate, for picks 5-24, the average wins is 80.

The average win total for selected draft positions...
Pick 1 average wins was 81.4
Pick 6 average wins was 81.3
Pick 10 average wins was 80.8
Pick 17 average wins was 86.2
Pick 20 average wins was 84.4
Pick 24 average wins was 80.8.

thejuice6 does a really good job making his themes fair to those that enter late.

Here is a list of the top 16 teams. The right-handed column is the pick#...
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Rank	Team Name	League	Owner	Wins	Losses	Pick#
-----------	-----------------------------------------------------	-----------	----------------------	-----------	-----------	-----------
1	BOS 1912-56, Williams x 2	4	schwarze	108	54	17
2	07-60 White Sox	9	Jtpsops	105	57	3
3	Chicago White Sox (1905-1958)	9	pedrocerrano	104	58	15
4	16-08 Two Chuck Chuck	6	redcped	103	59	19
5	CLE 1907-48, Joss x 2	7	schwarze	103	59	3
6	09-37 Pete and Re-Pete	9	redcped	102	60	22
7	Cleveland Indians (1956-2020)	7	pedrocerrano	100	62	8
8	PHI 1917-09, Klein x 2	6	schwarze	100	62	20
9	79-16 Vote For Pedros	4	redcped	100	62	15
10	1961-2004 Braves	10	kstober	99	63	3
11	Atlanta Braves	10	darny10	98	64	24
12	06-37 Joe's Got a Babe on Each Arm	1	redcped	98	64	14
13	NYG (1906-1927)	2	markeking	96	66	14
14	STL 1948-00, Musial x 2	5	schwarze	96	66	4
15	65-09 Barry Bonds' Celebrity Walkathon	2	redcped	96	66	11
16	Juice Red Sox (1957-2003)	4	calhoop	96	66	3

Ups and Downs...

Out of 20 teams in the first round, only THREE of them made their particular league's playoffs. Bleeeech...

Of those three, however, all three made it past the first round. Fantastic!

Then those three all were eliminated in the second round. Bleeeech...

Posted by thejuice6 on 9/20/2021 1:52:00 PM (view original):
Ups and Downs...

Out of 20 teams in the first round, only THREE of them made their particular league's playoffs. Bleeeech...

Of those three, however, all three made it past the first round. Fantastic!

Then those three all were eliminated in the second round. Bleeeech...

Despite having 5 of the top 15 teams, I only got one team into a WS. Playoffs are unpredictable.

It's pretty much a given that the average number of wins by the World Series participants will be lower than the average number of wins by all playoff teams. It's one thing if it happened occasionally, but it happens ALL THE TIME. I mean, what's the point of crushing the regular season when it's a near certainty that your dominant team will lose to some mediocre team? Check out these numbers from this tournament...
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League 1
98, 91, 91 win teams eliminated (World Series features 90 wins vs 88 wins) - Both W.S. teams are wildcards
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League 2
96, 96, 95 win teams eliminated (95 wins vs 82 wins) - Wildcard vs #3 seed
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League 3
95, 94, 91 wins teams eliminated (89 wins vs 88 wins) - #2 seed vs #3 seed
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League 4
108, 100 win teams eliminated (96 wins vs 93 wins) - #2 seed vs #2 seed
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League 5
96, 95 win teams eliminated (89 wins vs 87 wins) - #2 seed vs wildcard
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League 6
103, 92 win teams eliminated (100 wins vs 88 wins) - Wildcard vs #2 seed.
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League 7
103, 100, 95, 94, 93 win teams eliminated (84 wins vs 81 wins) - Ridiculous (#3 seed vs #3 seed)
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League 8
93 win team eliminated (90 wins vs 84 wins) - #2 seed vs wildcard.
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League 9
105 win team eliminated... Finally, a league where two *good* teams are in the World Series. 102 wins (#1 seed) vs 104 wins (#2 seed)
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League 10
99 win team eliminated (98 wins vs 93 wins) - #1 seed vs #2 seed (reasonable)

So, out of twenty #1 seeds, exactly two made it to the World Series. Four teams with 84 or fewer wins made it.

At least in this tournament there is a big reward for regular-season success. But if those results are the norm in all leagues, then something is a little off for sure.

Depends on team makeup too. There's often been debates about whether to build a team that can win 100+, or build a team that can sneak in, but dominate the playoffs. In the playoffs, you can drop your 4&5 starters and even use low IP SPs that you've been using as relievers in your playoff rotation. I do agree it probably happens more in WIS than it should, but each instance needs to be assessed individually.