GB Girl has some good advice there
I started with a 27, and at times, and not even 'big' weather, I had found myself crossing the broads and thinking "glad I'm not in a smaller boat". Now with my 38, I just smile and enjoy the splash in the face as the wind blows the water past my bow.
Also, it's a dual edge sword (as she says) when trying to find dock space at the public docks. Many times I've waited a while for room, or if the wind was too strong, just pass by and come back a different day, rather than wait for a spot, as with the wind, I would only consider one side of a dock to not chance banging up my or some other boat.
In the end, I'm much happier with my larger choice. Oh, except when gas was over $4 per gallon!