Sounds like a lot of fun, I'm glad you caught a good one!! That would be cool if they recreated a Michigan show tonight!
As for Jam in the Sand, I haven't done that, but the same travel company does Mule's Island Exodus at the same venue which we're going to for a second time in January because last year's was so perfect. So I have no doubt that the DSO run would be just as fun and definitely money well-spent. It's really like a private party, not a big crowded event like Paradise Waits. My dream trip would be to go for 10 days and do both Mule and DSO back to back. I'll meet you in Jamaica!!