Oh dear... I can imagine him being something like Eeyore, actually:

“It's snowing still," said Eeyore gloomily...

"And freezing."...

"However," he said, brightening up a little, "we haven't had an earthquake lately.”

(A.A. Milne, The House at Pooh Corner)

@courtenay  

Oh boy. I can hear it now:

"Forecast for the week looks alright, but there'll probably be a horrible flood this weekend, I shouldn't wonder."

"The radar says it'll be clear today, but I shouldn't be surprised if there's a blizzard later on." 

"Well, there's one good thing about this hurricane... we shan't have a drought." 

@the-mad-poet

I am in the state of Oregon, so we're known for constant rain. Puddleglum would probably be like-

"The forecast says rain, but I shouldn't wonder if there's any more, as Oregon is known to be."

I can almost hear Puddleglum saying, "The forecast says it's calm at the Eastern Ocean, but there will be high tides, I shouldn't wonder!"

Getting heavy rain in the State of Oregon. Puddleglum would probably say on weather channel, "The forecast looks fine, but it will probably turn to heavy rain."