Singlehand question on buying new boat
It is hard to answer that question for you without knowing a lot more about how physically fit you are. I don''t know if this will help, but I can tell you what I went through in my search for a cruiser that could be single-handed. I tried a lot of boats ''on for size'' meaning that I went out on a whole range of boats and looked at what I could handle easily and what was more than I wanted to deal with. The largest boat that I sailed on was a J-160 (53 feet) I can''t afford anything this large or new but I felt that I could single-hand the J-160 with the help of its electric winches but that single-handing something that size was not something that I would want to do in the confines that I was sailing in. Without getting into any detail, my own conclusion for myself was that 10,000 to 13,000 lb boats were much easier to single-hand than boats that were slightly heavier and longer. I ended up buying a fractionally rigged 38 footer with a design weight of 10,500 lbs and have found that to be a great platform to single-hand, slipping out for quick daysails almost as easily as on my previous 28 footer. My boat is set up to be an easy single-hander if you are in reasonably good condition.
When you talk about jumping to a masthead rigged boat of the weight of the 393 that is a pretty big jump in the efforts involved in sailing the boat. The sails are necessarily larger, and the jibs are huge. Each tack just plain takes a lot more energy. Because you can''t depower as easily, you are stuck making more sail changes or dealing with having a less than optimized sail size and/or shape for the conditions, either of those choices make single-handing more difficult a masthead rig more difficult.
I would definitely avoid in-mast furling and go with a two line slab reefing system because when you are single-handing you need to be able to reef reliably and quickly and in mast furling can and does jamb. Getting one unjambed is a multiperson project, and by definition you don''t have multiple people when you are single-handing.
On the other hand, I am in pretty fair shape but I am 53 year old, 5''9" and 165 lbs. A younger, larger person might shrug all of this off and be completely comfortable sailing a much larger boat. I had a 60 something year old friend who routinely single-handed his 42 foot, 24,000 lb boat, albeit he motored rather than sailed a lot more than I would ever prefer to.