For mine, the key question in deciding between a sailboat and a trawler is "How far do you want to go?".
A trawler would be great for short trips with a lot of marina or even
anchoring time in between.
Sailboat could be better for longer trips.
Trawlers look to be sought after at the moment with the good ones getting top dollar. Some of the newer big sailboats look to be value for
money.
Catamarans may suit your
family, but the better ones do attract a premium
price.