Hold on, I have no experience with power boats but I do have experience with boats.
I have never crossed an ocean, that's true, but I have done my fair share of sailing on sailboats in the Mediterranean Sea and in the Baltic Sea. Of course distances are shorter and weather conditions different. I like it. Even when it rains, it's cold, windy, there's ice floating on the surface and water gets on the deck. (And I haven't completely ruled out a sailboat from the back of my mind yet. Valiant 40'...love it)
As the title says, I'm looking for pointers. Of course I will need to try it (chartering), of course I'm not going to buy it blindly. I just want to make some research before I start chartering random boats.