Had cuddys for years. We very seldom actually slept in them. If I could find a 20' C-Dory at a reasonable price I'd buy it right now. Unfortunately they are a Northern boat dealer and pretty rare in Texas.
Cons.
Keep in mind, the design takes up a lot of your boat's deck space. Our 22' barely had room for three to fish.
They are prone to mildew. Store with a dehumidifer in it from time to time.
Deeper draft than other hulls such as bay boats.
Takes more power to get up on plane than other designs.
Heavy for their length.
Putting kids in the cuddy with the boat rocking is going to lead to vomit, every time.
Anchoring means having to skinny forward along the cuddy up to the anchor locker. It's best to have a powered rig you can work from the console.
Pros.
Absolutely the best rough water boat design out there.
More storage than you will ever use.
With the Isinglass enclosure, it's practically a floating RV in winter.
Excellent trolling platforms with outriggers.
Self bailing decks. (comes in very handy for washing fish blood and slime off)
Usually a huge fuel tank, live wells and fishboxes. Incredible range.
Can be rigged with twin engines or a kicker motor.
Easy to set them up for shore power if you want to overnight.
One thing to note. Key West is a popular and sturdy brand, but the more important issue is the motor. Since cuddys are almost always salt water boats I'd avoid any engine over 7-8 years old. Look very closely at the trailer as well.