I took a quick look at the Milwaukee Community website. They're affiliated with US Sailing, which (I believe) is equivalent to ASA in the eyes of charter companies. So I think you won't even need to challenge. (I got keelboat from US and my cruising from ASA, not much difference IMHO)
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"... the only matter of consequence before me is what I will do with my alloted time. I can remain on shore, paralyzed with fear, or I can raise my sails and dip and soar in the breeze." - Richard Bode, First you have to row a little boat (pg. 94)