Paul, I have no knowledge of lake Michigan and its conditions. My wife and I have a 365 with the 1.82 keel which we have owned for 16 years. I have sailed many different boats over the best part of 60 years. Most boats can be tender if one doesn’t reef down to suit the wind and sea conditions.
When we go out into The Solent to go west with the ebb tide, it usually involves tacking against the prevailing SW wind. We tend to put a single reef in the main as a precaution before we exit the river where we keep our yacht, as the sea conditions can get quite lumpy. Our yacht then goes well with only the two of us on board. It is then easy enough to shake out the reef if we need more power and if conditions are less severe than I had anticipated.