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Personally hate the look of flared handlebars, but again, I haven't tried any so I can't comment on the feel.
I prefer sizing up with the bars that I have on my road back. Ex 40-42, 42-44.
As for gearing in your area, you'll be fine with 44t, however I'd prefer 42t (my fitness sucks). But with a 42t, you'll be able to play with 42 and 46 cassettes comfortably, especially if you'll be bike-packing.
FWIW I've been on 42F/42R with 650b, and 42F/46R with 700c
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