Are you looking at an Alerion 28 for your 1st boat? That's basically a very expensive day-sailer. I don't think it is really set-up to be a comfortable boat for cruising, what with the very low headroom in the cabin. I think they made that boat specifically for day-sailing performance and beauty, with the emphasis on features above deck, not below. Don't get me wrong, it is very nicely appointed below-decks, but they consider the comfort and space below decks to be secondary to the sailing characteristics and aesthetics of the boat.
The jib boom is intended to make the jib self-tacking ... just steer the boat upwind from side to side and let the sails switch sides without having to adjust any sheets. Tartan also utilizes this feature on their boats ... but it can only be used with non-overlapping head sails.