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Well, thank you for all the thoughtful responses! As a follow up, I'll let you know we decided on a 9' AB w/ aluminum floor. The weight of 75# is acceptable to my aging winch cranking arm and our 8HP Yamaha is a good match. We decided we are willing to detach the staysail stay and sacrifice that sail option to make extra deck space for days we can't / won't tow the dink. Lord knows the Yankee was all we needed last season in Bahamas! Hopefully we've made a good decision. I think we will be looking into a mattress pump, as that's a great idea!
Another option is to keep what you have and tell Bob to swim to shore!

Miss you guys. Hope you are doing well. Kick Bob for me.

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