Where in Upper Michigan?
I sail a Catalina 22 out of the Houghton / Hancock area. We have a small club with members sailing everything from small beach cats to 30' plus racers. I've seen at least one Flying Scott for sale in the Marquette area, which also has some sailing clubs. Also sailed a sail fish / flying fish in some of the inland lakes near Copper Harbor (wouldn't want to take it on the big lake unless it was an exceptional day). It's a fun boat, but not suitable for more than 1-2 people.
Closer to the Wi border, you can find a lot of boats for sale in the Green Bay / Menominee area.
As for the type of boat, it's really hard to say. On inland lakes, or the Portage Canal, etc. you can pretty much sail anything as long as you watch the wind. Venturing out into the big lake (or lakes, depending on where) can be fun, but conditions make a difference. If I was only going to day-sail, I think I'd pick something with either a small cabin, or no cabin.
Small cabin can be nice for keeping gear out of the weather, and providing female passengers with a place to use the head (all we use on my '22 is a 5 gallon pail with a camping toilet seat on top, trash bags and some gel powder). No cabin means extra cockpit space.
Something with a retractable keel / centerboard is nice for inland lakes as they can get shallow quickly. That will also help with launching. Anything with a retractable keel / board means that you can pretty much launch on any ramp a power boat can.