Newbies buying 1st sailboat
First of all welcome to sailing. Sailing can be the most wonderful ways to spend time. We each come to this sport with our own goals, tastes, and personalites so that there rarely a one size fits all answer to any question that might fall within the broad spectrum of activities loosely grouped under the name of ''sailing''. I will try to give you the advice that I would give anyone but because I don''t know you it may be the precisely correct answer for your specific needs.
First of all, I basically agree with you that of the three big boat builders Beneteaus does the best job from a design and build quality standpoint although that can vary from model to model as each manufacturer has built some real winners and some real dogs. I basically like the 393. They seem to be good boats all around, although I much prefer Beneteau''s First Series both on build quality and sailing ability. But that is perhaps putting the cart before the horse.
As I said above, we each come to sailing with different goals. For some, it is not all that important to really sail well. For that group, it is good enough to just be able to get the boat out of the slip and with some degree of reliability, get out and get back. There is nothing that is universally ''wrong'' about being that kind of sailor. But for many of us, it is important to really understand sail trim and boat handling. By doing so we get a lot more out of the boat. It is not all that difficult to develop the skills that make it easier sail more easily at either end of the wind range, sail with less heel and a more comfortable motion, and sail faster. It means fewer engine hours and more sailing time.
If you fall in this second category where you really want to learn to sail well, I would suggest that having taught perhaps hundreds of people to sail in my life, it is almost imposible to learn to sail well on a boat as big as the boats you are considering. It sounds like the sailing club that you belong to have a range of boats available. I would suggest that starting out you spend a lot of time on boats that are ideally 22-27 foot, light weight, tiller steered, fin keeled, fractionally rigged sloops. I would also see if you can get a knowledgeble racing sailor to come along and coach you a bit. It is not that you can''t learn a lot on other boats or without coaching, it is just that boats fitting that description provide a lot more feedback and generally have the tools to help you to quickly advance beyond a rudementary and very basic understanding of boat handling. If developing a high level of sailing skill is not important to you then don''t worry about that advise. If you do follow my advice, you could easily end up buying a different boat than you are currently considering.
As someone who has single-handed a lot of boats, I would suggest that 15000-16000 lb, 37-38 feet is handy size to short-hand but above that boats become rapidly harder to handle on your own. It is not that they can''t be handled, but as boats move beyond that general displacement range it becomes harder to do as loads and the needs to be in two places at once go up quickly.
If I were doing what you are proposing I would seriously look at the Beneteau 40.7. While they are not as commodious as the 393, the 40.7''s fractional rig, better structural design, hardware and deck layout make more sense to someone sailing in your venue and doing a lot of single-handing. Fractional rigs use smaller headsails and can be more easily depowered (rather than shortening sail) than a masthead rig.
As to in mast furling, I really agree with your assessment. I think that you would be far ahead with a conventional track system and a two line slab reefing system lead back to cockpit. I frankly consider in mast furling an unsuitable rig for single handing based on my own experience with them jambing at key times and from my conversations with sailmakers who say when being candid say that they result in poorly shaped sails when partially reefed and greatly shorten the useful lifespan of a sail. And yes there is a major performance hit which in the prevallent light air of the venues you have chosen would mean a lot more motoring and a lot less sailing.