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The key is to making it easy.
SUPing isn't meant to be hard.
This is the problem - the first decision we have to make is whether we agree with the above statement. If you want it to be "easy" then the board choice is much easier. But I am sure that is not what got this thread started.
I see lots of comments from the "apex" of the sup community - they are pushing the limits - which is fantastic. But if you compete, surf a LOT, have deep pockets (or are sponsored), then the situation is quite different to 95% of the sup market.
So when you want to push the limits you have to somehow assess how the combination of length, width, shape (esp. nose and tail), rail shape/profile, materials used/board weight, rocker, and other factors will make your board perform - which includes the question of stability.
All we have to go on is some marketing blurb and videos of pros riding the board - pros who can make an ironing board look good.
For 90% of us, renting/demoing is not an option. And besides, if you are choosing a board near your limits, one demo session in whatever the conditions happen to be at the time is not a 100% indicator of how it will perform for you longer term.
As an engineer, I would love the industry to adopt a modeling process - model the yaw, speed, stability (cross and end-to-end), ability to take a drop, maneuverability, etc. - and to do that with different weight riders. Only then could we compare apples with apples. But like I said, I am an engineer.