with the low transom deadrise I bet twin 300zukes would give that 36 Judge a cruise near 30mph. Bill Judge gets a 28 knot cruise with single 425hp cummins on his personal boat. Remember Judges are all made with light, top shelf, composite materials like Nidacore and Divinycel. See here:
personally, If I cant trailer it I would say give me the big single diesel with a bow thruster and get it loaded to the 9's for under 250k. It is the old williams 36 mold so it is a proven hull too!
I've seen several 30' to 40' boats in the southern Chesapeake region that are available for less than $20,000, but the boss says "No!" She won't allow me to buy any boat that is wooden.