Sorry, I can't really help. Vacuum cleaner horsepower rating are even MORE bogus than pool pump horsepower valves. "Big" means "big enough to do the job", and unfortunately, horsepower numbers supplied by the marketing departments of the vac companies are just misleading. What I always used was a Mighty-Vac, but apparently they are no longer made: https://www.amazon.com/dp/b003wlcj9o
This may be the current replacement: Air Supply Florida Cyclone Vacuum and Blower (@ Amazon)
I've already given you the best advice I've got, and I'm not going offer uninformed speculation on something as critical as properly winterizing a pool in Connecticut.
Sorry.
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