I just drove through Canada recently heading back to Michigan and was thrilled to grab a couple Coffee Crisps. Windsor is such a nice town. I have so many fond memories of partying there when I turned 19.
No, that's a long drive and while it is more leisurely, you lose days when you have to stop overnight or you're dead tired if you drive straight through (I've done both). But honestly, flying isn't that bad. If you cross into Detroit and depart from the McNamara Terminal at DTW (which is gorgeous), there are several flights that go to Orlando from Detroit every day and are nonstop. While MCO is a bit hectic, I've been through much worse airports (Frankfurt is insane). If you are worried about the drive or the traffic, I'd seriously consider giving flying a try.