I raced a Heritage One Ton (38 ft)for many years with a mixed crew of 6 to 8. It was a croud. We often talked about cruising that boat but with the IOR nipped in stern and long narrow bow it would have been like camping. there was a 41 footer near us with a hard chine and about 6" of cabin height. The hard chine stretched the flat part of the cabin floor a lot. the transom was broad and the inside of the boat was a palace. I am really impressed with the volume and comfortable space in the modern smaller boats with the wide transoms and beamy interiors. Some of the recent 30's hold way more space than a lot of the older 40's. There are many people cruising boats smaller than 30. There are many options here and what you intend to do with the boat makes a great difference. Will you day-sail? coast-wise cruise? island hop? circumnavigate? How much fuel and water will you need to carry? How much pantry and refrigerated space is enough?
We intend to cruise extensively off shore so we went for space and mass. Our Camper is 58 feet and displaces 55,000. It has a full keel with swing centerboard and skeg mounted rudder. It is packed with amenities but it was fitted out to be crewed by one or two. We plan to have our kids and grandchildren join us part of the time. When we decided to retire it was either a large place in Naples or this reltively tiny little boat.