One of the common problems with the Cutlass 27 sailboat is that the interior is very plainly finished and small compared to more modern boats. Some owners may find the lack of space and amenities uncomfortable or inconvenient for longer cruises.
Another problem is that the boat is significantly under-rigged, meaning that it has less sail area than most similar sailboats. This can affect the boat's speed and performance in light winds and may require more frequent use of the engine.
A third problem is that the boat has a long keel, which makes it more difficult to handle in tight spaces or shallow waters. The boat may also have more drag and less manoeuvrability than a fin-keeled boat.
These problems are not necessarily deal breakers, as they are balanced by the boat's many positive qualities, such as its beauty, stability, comfort, and seakeeping abilities. However, they are worth considering before buying or sailing a Cutlass 27 sailboat.