It's size.
I'm very familiar with the capabilities of an H-27 Cherubini having myself owned a 1983. I would be concerned with the following; 1) Deck to hull joint. 2) Spade Rudder makes for a weak design. 3) Deck Stepped mast. Riggin will sag under compression. 4) Low companion way entry step will allow water into the cabin. 5) Small winches. Can't even hoist someone up the mast. 6) No refrigeration. 7) Limited space for provisions. 8) No shower. 9) Shallow bilge. 10) Replacing hatches and portholes, through the hull valves, packing gland, cutlass bearing and rigging. Replace all halyards and sheets and start with good to new sails. Replace all blocks, add a traveller and reseat through the hull transducers. The H-27 Cherubini is a production boat designed for coastal cruising. Its ability to to handle foul weather is limited by its size and design. This was the least expensive boat of its size in those years as you can see by the size, quality or lack of components. The money to be spent in upgrading the boat would be best spent on a bigger boat. The rule of thumb is that to cruise offshore you would need a boat of at least 30 feet. The boat is at it's best as a weekend cruiser in protected waters. It would be great for the Long Island Sound but I would not take it to Bermuda.
