What is the maximum draft you want?
I usually feel like a novice on these forums, however a downeast with an outboard is an area of interest for me. One of the things I appreciate is a shallow draft for the type of boating my family does.
So there is rumor that Steve Law built a larger SeaWorthy with an outboard. See
this thread.
Another alternative for a larger DE with an outboard is the Flowers South Shore 30'. Although I believe they only made one, and the the buyer has had health issues and never finished it. See
this thread. I asked Ken about the draft, and he thought it would draw 28" if I recall correctly.
I know you said 28' was the minimum size you were looking for, but a used DE with an outboard was a 26' Sisu completely rebuilt by JoFishes a couple of years ago. He is looking to sell for what I believe was $35K if I understood him properly in
this thread. This looks to be one of the biggest 26'ers I've seen. Looks to be a solid rebuild documented in
this thread.
I hate to point this out on the DE boat forum, but you may need to consider a Chesapeake Dead Rise if you want a good sized cockpit with an outbaord, that draws little water. I wish I could find a DE that compares to the
Judge 27'. I just wish I could buy one and install a flowers pilot house, as I think that the house on the judge is fugly compared to a DE. However, it can get into very skinny water, and can be fast and economical with a single outboard.
Again, smaller than you wanted to go, but a BIG-LITTLE outboard DE style hull that draws a little water would be the
Rosborough 246 Custom wheelhouse, which is a favorite of mine.
Well that is all that I know of such a beast after looking at these boats for years. Anyone with any other opinions I'd love to hear from.
Good luck in your search!