Milwaukee is the bee's knees. Check out some recommended things to do on this custom map: https://www.google.com/maps/d/edit?mid=1I9RxNPujijtYy8GEHTqWl7KwKJTHeQM&usp=sharing
Yes, the caterer will provide vegetarian Italian dishes.
I don't know ask Rick
If you book tickets early, you can get roundtrip non-stop tickets from Boston to Milwaukee for less than 200 dollars. As you get closer these prices can reach the 250-300 range. A typical hotel will range from 200-400 a night depending on how fancy you want to be. AirBnB's with multiple guests together can be really nice and a great deal. For instance, this AirBnB in Bayview will be about 500 USD for the weekend and sleeps 6: https://www.airbnb.com/rooms/13388506?check_in=2025-09-19&check_out=2025-09-21&guests=1&adults=1&s=67&unique_share_id=704be370-b885-404d-94c2-4733eb7e3917
Yes there will be an optional welcome hangout at the South Shore Beer Garden on Friday September 19th starting from 5 pm. Feel free to drop by and stay as long or as short as you please. Food and drinks are available for purchase.