So your saying even if you are an experienced sailor you should not sail a new boat, because you would not have the experience to sail that model. Sailing skills are in no way transferrable amonge mono hulls?
Many people sail south (from east coast US) in November, as long as the weather predictions look positve for the trip. Remember, Marine Flower happened 20 years ago, weather predictions and ship board electrionics were no where near what most skippers have today.
Contrary to what you post, I am not painting a picture of the Dashews being frail. Quite the contrary. I am amazed at the Dashews, their skill, their knowledge, and their talents to design a spectacular blue water boat. If I were going to purchase a boat in the 60+ foot range, it would probably be a Sun Deer (in fact asked my wife if we could sell our house to by the Sun Deer now for sail on Kauai- she said no...) I was not familar with the Dashews or the Sun Deer until this post, and thank for providing the information. I am also in the process of purchasing the Dashews publications- these are the best I have ever seen. I am awe struck that the Dashews- sailing ability, nautical design, and able to put all of this is writing. Truly amazing sailors, and in my mind, probably the best in the world.
The Marine Flower 2 had a crew of 4, if you include a wife with a newborn baby and a 13 year old girl in addition to the skipper. Effectively the skipper was singlehanding the boat once it hit bad weather. Yes, I think that is a mistake in the Atlantic at that time of the year. Interestingly he was sailing under main alone - storm jib and mizzen would have been a more logical choice - hove to possibly.
Steve Dashew's books are the best I have read relating to sailing from design to rig to equipment and its installation. They have no equal as far as books by designers as far as I know. I do not know of any designer that has several hundred thousand blue water miles to their credit. The best is the Offshore Cruising Encyclopedia, 2nd edition. I have both editions, as well as his other books. A major part of the book relates to building a reliable boat that doesn't need the kinds of electrical/mechanical aids that are common today on large (and small) boats. The Sundeer 60 is light for its length, lean (13'4" beam) with a long waterline (59' - Disp/length 82) and simpler than many 35' boats today. If the electric winch did fail manual would work well with a rig that is simple and easy to handle. The only other "complicated" sailing equipment are the jib furlers, well proven by 1994. Its sail area is comparable in size to many 40 to 45 foot boats. Yes the anchors are larger - main anchor over 100 lbs on many. Most boats over 30' have an electric windlass and they are very reliable, if in doubt install 2 like a friend has on his Maple Leaf 50. They were designed to not need bow thrusters, now common on much smaller boats - their spade rudders are oversized for easy maneuverability in marinas at the expense of a slight loss of speed in light air, with rudderposts that are also oversized. Yes they have a lot of electronics and a reliable autopilot - Steve preferred the W-H autopilots which are one of if not the most reliable, still uses them on his powerboats. Some also have wind vanes. With more sail area the winches and deck gear is more capable as well. They could be sailed if necessary with manual winches and a hand held gps if all electrical power was lost, an unlikely event with well designed and built systems that are easy to service because they are not crammed into a small space where service is difficult.
Paulo has posted about many modern boats that rely heavily on items like in mast or boom furling and electric captive winches for the mainsheet and other aids that are more complicated than you will find on a Sundeer. They are really quite simple boats for their size with reliability first and foremost.
If I was going to buy a Sundeer now it would be Ocean Jasper, located in Maryland - I prefer its slab reefing to the in-boom furling on the one in Kauai.
One chooses the boat they are comfortable with that is within their budget. Whether it is a NorSea 27 or a Hallberg Rassy 64 or a Sundeer 60 it is their choice and their choice alone. Personally I would take a simple large boat (Sundeer) over a complicated smaller boat anytime. I think my ideal would be an aluminum Sundeer type boat in the 50' to 60' range.
As far as losing an anchor - it is very good seamanship to buoy an anchor for later retrieval.