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I definitely want more of a bare trunk than tapered foliage. I almost wonder if what i'm looking for would lean toward a literati style. i.e. tall and lean with foliage at the top)
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And you want deciduous too. Sounds to me like Bald Cypress is your tree. They are very easy to grow and if I'm not mistaken pretty much disease and bug resistant. They grow in swamps and to a certain degree in drought like conditions so they aren't finicky. I have read they grow as far north as Wisconsin too so cold weather is apparently not a problem either.