With a minimum of effort the Hunter 26.5 can be raced in mixed fleet racing well.
I liked the layout of these boats as you mention.
This boat won't require winches for the spinnaker if you put ratchet blocks behind the primaries.
This will NOT compete head to head with an S2 7.9, but can outpace a 25.5, and the catalina 25 quite well. To beat its own rating you'll need to equip it with at least radial sails and you'll need to do acceptable symmetrical spin work. If you race JAM, this boat will mop up off wind, except DDW. Getting point out of the boat will require you to sail smarter, by feathering upwind.
Check, because I don't believe they made anything other than the wing keel model.
Because of the mounting location of the tiller, you must get crew outward earlier. These boats overpower early, and dig in, so they need to be flatter than you would think to get proper speed. A good analog knotmeter will be a requirement, or at least one that updates quickly. When I say little heel, I'd say anything under 10 degrees.
We have had a local guy sail with our PA fleet, a 25.5 (smaller and slower than the 26.5) with inboard, who was VERY successful with the boat. He ran a cruising spinnaker, and radial sails. The boat kept speed with my Capri 25, with new sails off wind, where I killed him was upwind, and DDW. What is interesting is he swore the boat did well over on its ear, and he frequently sailed the boat past 20 degrees of heel. So maybe this negates my earlier argument, but he might have done better if he kept flatter.
Either way I always liked the Hunter 26.5 for a sleeper PHRF boat. Just don't expect to compete with Js
and such, but play the ratings game, and make sure you sail better than your own.
If you want to go crazy strip the boat to the minimum gear for safety (no cushions), and find a way to get that outboard off the stern while racing.