I started with a Hunter 260 and sailed it for 5 years. It had very little to assist me. Outboard engine, but wheel,steering. Had a roller furling jib. No windlass. We had a head but no real kitchen, refrigeration, etc. I had to straddle the companionway to get the sail down. We didn’t cruise it, just day sailed. Wife put up with it and we would spend one weekend a year on board.
After 5 years I asked her what it would take to really have an enjoyable boat we would use a lot. Bought a new 2003 Hunter 356 with Northern Lights 5Kw generator, tracking antenna with Dishnetwork TV, Full cockpit enclosure, Full time HVAC, full toilet with shower, hot water, refrigerator/freezer, microwave. Queen size Bed and gas grill. I got radar, sonar, chartplotter , belowdecks autopilot- all the latest bells and whistles. This boat was equipped like no other on Kentucky Lake. Had roller furling main and jib and electric windlass. I set it up to take to Florida. People thought I was crazy. Sailing was supposed to be tough, cold, wet, miserable, beannie weenies and Cracker’s. It was easier to sail than my Hunter 260. Today I have cruised this boat nearly 10,000 miles. My wife and I spend an average of 70 days a year onboard. We eat good meals in comfort and don’t leave the dock without the generator running and a 70-72 degree interior. We have a 6 month cruise from KY to SW Florida under our belt. We built the boat to use. Anything smaller would not have worked. We looked at a Hunter 42 and almost bought it, but the floor being several levels held us back. We thought as we got older we might trip and fall. As we start our 18th season - turning 73 this spring, we have new North 3DI cruising sails and all the original equipment is still,operating. We added AIS on our Florida trip. I essentially single hand it and my wife helps in locks and docking. Get what is comfortable and consult your wife. If she won’t use it with you, you will not have a successful boating experience and won’t use it. Size and comfort matter as well as equipment. Stay dry and out of the wind during the spring and fall and you will have many more sailing days. Make a bigger boat small with the right equipment.