I love wooden boats and for many years I have signed "Wooden boats" a great magazine if you like classical boats. There are some expensive building techniques that can provide a low maintenance but generally if more traditional methods are used they need a lot of maintenance to remain in top shape (I know I have recovered and owned one for years).
If I had the money to pay to a skilled worker to maintain one and the money to maintain it in top shape I would probably fall in love with one. It is easy to fall in love with a wooden boat, they have a soul while plastic ones are just nice boats.
Among the ones that design wooden boats, with a classic look but a modern under-body Stephens Waring & White are among my top list. Just look at some of the boats: