I don't know how much gust-force there is, and what size flag we are talking. I'm one to stack odds in my favor. Don't know what size Dave is, either. I'm guessing most serious skiers are fit.
I wouldn't forget I'm off the ground...I'd make sure my rhythm doesn't start the pole a-movin', like the thing to avoid climbing a dead fir top into smaller wood.
I'd want to know about load rating. You can always guy it three ways, midway up.
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