Thank you for the feedback.
I figured the money figure I threw out there was somewhat unrealistic for a boat on the larger side, say 30'+, but I was hoping that for that price we could get something good on the smaller side.
In the discussions we've had regarding getting a boat, my wife and I figured $5k/year to spend on it (plus storage, both in and out of the water) was a good safe figure to have to spend on upkeeping it. I honestly did not know the price for upkeep on a larger boat was that much - thank you for opening my eyes to it.
I have spent a fair amount of time on a 28' boat with up to 6 adults, and I found it comfortable and felt very safe. That was the basis for my 4 adults for an overnight trip. We're very used to packing light and camping in close quarters with others, so that kind of stuff does not bother us, but I also want to make sure that 4 adults (total combined weight of approx. 650 pounds) plus gear for a few nights would be safe aboard a 26' or 28' boat for on Lake Michigan or Lake Superior.
Also, thanks for the suggestion on a smaller boat, learning, and then working up. That's similar to what I did with power boats (started with a 16' boat when I was 16, and then worked my way up to the mid-20's), which taught be a lot about being on the water, operating safely, reading the weather, etc.
Honestly, 75% of the time on anything more than a day sail it is just going to be my wife and I, and the rest of the time it will probably be one other couple at most.
Is a 24 to 26 foot boat something that is safe enough for the above listed scenarios on Lake Michigan and Lake Superior?
I have been around power boats all my life, and in some cases I wouldn't think of going out on Lake Michigan in a 35' boat, but I have not been in rough seas very much on a sailboat. My most experience on rough seas came in a 28' boat with 5 adults on board, and I felt very safe and secure and was impressed on how a sailboat handled versus a power boat.