Back when I used to work
in the "boat industry" our marina was the US importer for a Swedish built boat
. Most people would go one size over the boat they could comfortably afford with all the bells and whistles and buy the bigger version, bare bones. It cost more to keep up and because it wasn't as well equipped they were not as happy using it....but they did have a bigger boat, to some people size matters. What I suggest is get a boat you can comfortably afford all around as well as handle. For my purposes I have the ideal boat, one I could afford to buy, keep up, big enough for me to live on and can comfortably take me a one crew member
where ever I want......There are many factors for what makes up the right boat for a person, there are quite a few costs that are set in terms of $/ft or x$ for <30' and y$ for > 30', plus some stuff just plain costs more for a larger boat, every componet that increases in size, the initial cost, cost of maintenance
, repair and operation increase...this is not just the boat it is everything related to the boat. A bigger boat is physically more comfortable (though under some circumstances a bigger boat is more difficult to handle), but if the cost becomes uncomfortable that defeats the purpose.