It's a shame you are having such a problem with this. As you have probably deduced, small boat captains simply hate the idea of someone without their pedigree being successful at what you would like to do. Long before you get to the point of needing to know what to look for in a specific boat or type of boat, you really do need to define as closely as possible exactly what you would like to do with the boat, where, and for how long. There are many boats available that make fantastic liveaboards, many more that make great inland cruising boats, and many more again that make really great platforms for island hopping in the Caribbean. Spend a lot of time defining your dream first, then look at the type of boat that most experienced people use in the situation you define. See if that fits for you. By the time you have that figured out you will have answered a lot of your own questions. Read books written by people like yourself who did what you want to do, in the US and in Europe or elsewhere, learn from them and their mistakes and successes. There is no hurry to choose a boat, there are plenty of them around and one will wait for you. Good luck and try to enjoy the process in spite of the admiralty.