First, Jon...Let's just all agree that no one asks someone to love you when you ask a tough question "in public" (or otherwise). But an unreasonable response to reasonable questions is by definition (and maybe by modus ponens) simple unreasonable. Some of the responses deserve an, "awe fuck you"...
Secondly, You (as many of try to) avoid didactic prouncements to an almost solitious level. Polite, however uncomfortable the implications might be, questions which are inherently posited with: "I wasn't there...", "I might have considered...", "We've all been in situations where upon reflection...", "They are more expereienced, so I'd like to better understand...", etc. DO NOT call for such reactions. When you get a vehement reaction in such circumstance from people, it belies some deeper issues.
Thirdly, when one reaises some questions, and someone responds you have reactions to each response: i) accept that answer as responsive and answered; ii) re-ask or ask a another question because it raised another matter in your mind; iii) ignore the qanswer because it was clear that person responding clearly either doesn't get it or just can't respond.
In this case:
o The explanation of the "Why did you ever go out then to that in that boat at this time of year?" was "We are hired guns. The Owner wanted it so. He paid us to do it, someone would, that's what we do, etc.)" is a direct answer. In retrospect, as you allowed, it didn't turn-out well. It doesn't deal with the matter of which course was elected or not changed from the original plan? (e.g.., bail to down the Chesapeake, and/or Intercoastal Waterway, or Bermuda). There are multiple variables: Course, time, and when to change the orginal plan -- withouth "not going at all".
o The explanation of why we didn't check the battery levels and do something about it, is simply "we didn't". I have done things that where the response to a question was "I didn't" -- that's a response which may be factual, but not of use as model for future approaches in such circumstances. (If you know that you have a new boat and you're on the wrong side of the Gulf Stream in the winter and the weather is pretty snotty, etc.) I have not paid attention of details occasionally in my life and suffered the consequences -- experience is like that, if you survive and/or someone else learns by it it may be a useful experience. That doesn't make my mistakes exemplary, just useful experience.
o The engine issues with the starter (and, for that matter alternators/regulators) they answered. I accept that you wouldn't be removing a starter motor from an operating Yanmar 30 diesel engine under way, in a pitching sailboat, and transfering it is a bit much for mortals who expect to survive with fingers, hands, eyes -- let alone succeed at not really doing it. I'm not sure why you couldn't swap-out the alternators or regulators? I'm not a diesel mechanic or an alternator expert myself. As for the starter failing, my guess is that it didn't fail. My guess is that the solenoid didn't have the requisite juice through the starting circuit to kick-in. The didn't describe jumping it with a screwdriver to check that. Anyway, when the boat floats up onto shore somewhere, maybe someone will determine what was really the case.
o I think the "we weren't worried about having battery power, we're sailors on a sailboat..." is a nice notion if you could sail, you could steer, and you did do that. Otherwise, I accept that the refrigerator isn't too important, but the communications gear and lighting and other basic needs are. If you can't steer, storms are coming, you can't talk to or call for help, etc. I think that answer was just a bit dismissive for me.
o The cut the rudder in half was clearly not too likely at sea withouth a bunch of tools and calm weather. (I'm assuming the tube wasn't light stock, but maybe I should assume that :^)))). However, the "why didn't you drop the rudder?" answer was amusing and indicative. Assume the rudder displaces the following average 2.5' (w) x 4.0' (d) x 4" (thick) = 3.3 CF. That's just over 200 pounds. (I know they have a bunch of steel in it and a 3' (punny) rudder stock too). Now if the dry weight of the rudder is 150 pounds, then they would only be pulling down 50 pounds or less. to "drop it". (If I were being snotty, I might suggest that boats rudder seems so inadequately stiff that you could have bent the jammed on back in place with simple dive, and rigging a line to a winch (which you would have to manually grind), etc.)
Finally, while I'm at it, I am so amazed by the soon to be owner of Hull #2. His committment and faith is a committment to many things. As an experienced sailer of a MacGregor 65 in the open ocean, he's used to living life without risks.
P.S. -- The wave piercing hulls of the Alpha 42 (with it's feather light rudder assemblies, in mind).