On the other extreme are the points raised by ... Paulo. Paulo rightly points at very large designs which are well designed and engineered to allow a couple to safely handle them in a broad range of conditions. These are truly amazing boats that demonstrate what the ingenuity of man can accomplish. But again, few of us can afford to buy one these, and frankly few of us have the skills that it would take to sail one of these well, and safely, and to repair any possible critical element that might happen to fail mid-passage.
And even if (and I know that is a big 'if') we can agree that these particular larger boats can be safely handled by a couple if properly engineered and equipped, that does not apply to all larger boats. For as good as these examples may be, the majority of big boats out there are neither designed, or equipped or even easily adaptable to being safely sailed by a couple.
And at the end of the day, the reality is that boats at neither end of the extremes truly make sense for any of us. In an ideal world, we have each analyzed our specific needs in terms of how and where we sail, comfort requirements, purchase and operating budget, need for speed, tastes, skill sets, and physical abilities, and purchased the exact right boat that is the precise mix of virtues and liabilities to unequivocally correspond to our needs. And that boat is precisely the right sized boat for safety. (At least, until our needs and our corresponding analysis once changes one way or the other.)
Jeff, agreeing generally with what you say let me clarify what I have tried to say regarding bigger cruising boats:
Older production cruising big boats (between 50 and 60ft) were not designed to be sailed solo or by a short crew. Today practically all cruisers, including mass production cruisers of that size are designed to be sailed solo or by a couple. I will not post about all the improvements in rigging and power aids that had made that possible since I am sure you know them. It is a question of design and technology.
Regarding the rest I want to say this:
The OP had sustained in generic terms
that smaller boats are not safer than bigger boats and I assume he is talking about offshore sailing otherwise all this would not have any sense.
The thread is a discussion about that assumption. He said on the first post:
"Over the last week, I have read a number of posts, here and other places, regarding not feeling safe in open water in smaller boats. Now days that seems to mean less then 35 ft!
How many out there equate size to safety? Does it have anything to do with it? If you think size does provide safety, why? ....
.. Dave Chamberlain... (sailed) a 20 ft. boat from the West Coast to Hawaii.
I have never understood how or why people equate size to safety."
The answer to this quite, objectively, is that clearly safety and seaworthiness of a sailboat has to do with size. We are not talking about any particular case but as the OP has putted it, generically.
This means that a 35ft designed along the same lines of the 27ft the OP sails, will be safer, a 40ft even more seaworthy and if for the sake of the discussion we would consider a 100ft, much safer.
Off course a 100ft would have to have an adequate crew to handle the boat but that as nothing to do with the point in discussion. I am sure that the owner of a 100ft will have the money to pay for an adequate crew.
The point is that generically, as the subject was presented, the OP is wrong:
The size of a boat has to do with its seaworthiness (not particularizing any type of boat), generically speaking. For the same type of boat the bigger will be more seaworthy and the reason is the bigger boat has a bigger stability.
Assuming that size has nothing to do with seaworthiness makes not any sense and it is dangerous as it is dangerous to assume that it is safe for a 20ft boat to sail from the West Coast to Havay or even that generically a 27ft boat is as appropriated to be used offshore as a considerably larger boat, generally speaking.
The discussion regarding if a bigger boat can be handle for one, two or three has nothing to do with the generic principle in discussion and is an altogether different subject that has much to do with the skipper experience, the type of boat and the way the boat is rigged.