There are some great articles on choosing a trawler at
www.nordhavn.com
One of the main points I remember is their advice to choose the smallest vessel that will suit your needs.
Remember that you will be manuvering the boat to get fuel, provisions, etc...
A boat that size will be difficult to get dockage for. The draft will eliminate many nice places to visit. I have a hard time imagining taking a boat that size around the great loop.
Having paid crew onboard might be something you can afford, but do you really want to loose the privacy of being alone on your boat?
At least you're thinking about it instead of just writing a check. Thats a good start.