Although 2 meter will have a extraordinary range when there are linked repeaters--there are many remote areas--including Lake Powell, the Yukon, parts of the Inland Passage, most of Mexico, the Bahamas etc, where you need ham SSB. I can say that running the East Coast ICW--there are 2 meter (and 440) repeaters with good coverage. But the time you cannot get 2 meter may be when you need help--and there are plenty of ham nets to get you that help. There are also a number of boating specific nets--4 at least for Baja and Sea of Cortez, at least one Central America. Several for West Coast, and Pacific Boater's Net (Port Ludlow YC) for Washington and BC--one up to Alaska Boating nets. If you want to communicate with the other C Dories that are cruising Alaska, the best bet is to get on an Alaskian boaters net with SSB.
So you get the general license--all of the questions are on the internet--you just have to learn them--but I really recommend a junior college course in ham radio and really learn the fundimentals, rather than learning to a quiz.
The ground as I noted is the most difficult issue--but certainly not at all impossiable. I have rigged a number of both power and sailboats, which have world wide communications with marine SSB.