I agree with Mr. Ado.
It could be a bear of a dilemma, but your guest is a gentleman above all. Surely he is acutely aware of the problems his size can present. If you were to discretely ask him if he thinks the chairs are adequate, he will certainly understand that you simply want everyone to be comfortable.
p.s. "... somewhere between 273 and 296 lbs."? Boy, are you good!
p.p.s. Looks like maple.
.
I imagine those chairs will be all right, if they are blocked at all four corners underneath. They look like reasonably constructed medium scale solid wood contemporary dining chairs. I've had this problem too, if in doubt just get the guest a sturdier/more 'disposable' chair and don't worry! It will likely be appreciated anyway, "A big man needs a big chair".
So yes, big person, please sit on this Aalto stool, not this DCM! If there are multiple choices a self selection process seems to happen too, which is convenient if you don't want to have the discomfort of a brief session where you teach your guests how and how NOT to use the furniture.
I have forbidden people from sitting on the furniture before, I'll take the guilt of it over the very likely possibility of broken springs, etc. But I'm a bad person, ya know-
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