I saw that ad for Boomerang as well. Pretty sure there are old threads here involving that boat.
The Fales/Willard boats were my first choice when I was looking for an inexpensive loop boat. Everything else I considered was sort of benchmarked against that boat. They're scarce though, and some are pretty tired.
As Frosty mentioned, I did the loop in an old Mainship 34. It had more comforts than I had set out to find, and served me well. But I was largely solo and have pretty low needs. I really liked the boat. Good choice.
Any boat in that price range is going to be a compromise. I'd argue for small. The older European boats like the Albin 27 could do the trip quite handily and economically, and are comfortably in your price range.
