Hi Donna, I'm a local here at Virginia Beach and your going to find most live aboard marinas are in Portsmouth and Hampton areas. They also have limited space available. Another option you might look at is being a boat sitter over the winter to see if you are going to like it before buying. Some with large boats will rent them over the winter to have someone on board. Although they are not easy to come by.
Also as Chuck said, you don't have to learn everything at once. You can find a boat, get a good survey and if acceptable buy it and move aboard. The learning curve can start from there.