Hey there, I'm from Michigan as well. My
advice (if you have not already done so), go
charter in the different spots the types of boats you would like. We've done catamarans and mono's both, had a blast each time. So far we've done
Bahamas, BVI's twice, St. Vincent & the Grenadines, and the Swedish archipelago twice. This fall is 2 weeks in
French Polynesia, and next year is
Croatia and
Greece. What a blast, plus definitely gives us a good idea of the
trade off's on different boats...all for way cheaper and less hassle than actually owning a "newer"
boat. We will probably end up on a 45ish foot owners version cat once we pull the
plug. Mono's though are way more fun for the first few hours of sailing that is for sure, but the boss is making the decisions!
Good luck!