Whoops, I keep forgetting our cups are based off of random statistics

In that case, more games played is neither necessary beneficial nor detrimental for Cup status, as I'd say many teams often don't even bother aiming for the Cup qualification statistic until they know they're out of the running for a top seasonal place, or close to not qualifying for the Cup. Still though, more games would mean that a season champ is truly a season champ.
Some more musings:
One weakness of longer seasons I forgot to mention was a higher barrier of entry for newcomers. Longer implies less casual, they'd probably be trying out a new team (who they don't necessarily like), and they wouldn't be used to losing. I'd definitely say if we ever try a longer season, it never be one where we have any newcomers.
A strength I didn't mention lies in player development: The longer a season, the more interesting levelups become. Not by much, but a tad bit. This is because you can develop your players more to counter and to target other teams. You'd get to play a team at least once before facing them again. This could let you realize that one weakness of your team against them ("if only I'd had tackle!") and then you can tool against that specific team. It encourages rivalries and stories, too (I'm 100% win rate... except for that one damned game against the vampires! I'd better take tackle!)
You can still tool and hard counter in a shorter season
if the scheduling works out and you're given time to get the experience but it's less pronounced and theorycrafting isn't as much fun as the experience of playing a team and knowing what needs doing.
Of course, the % of games where a taken 'counter' skill is useful vs non-useful wouldn't change... but it'd feel more impactful, given that should you choose to play that same team in the next season you have no idea whether said taken skill (like tackle) will be useful or useless. Countering specific teams becomes less of a crapshoot.
-------
I'm firmly in support of a longer season, but despite all my wondering words it's not too important to me. My theory is that if most of us are still playing in say, two years, we'll have tried out a decent variety of teams and each have a small catalogue of developed teams to pull from. Then, if we do try out a longer season, we can each bring out a team we know we love playing.
Besides, shorter seasons just means the goblins have a higher chance of taking home a trophy.
