R, there are several interesting, complex questions wrapped inside your short post.
To start at the end, buying a smaller boat doesn''t mean you''re buying a simplier one. (To see this illustrated, visit http://delezynski.tripod.com/Guenevere/id6.html and consider that Greg has just purchased yet another huge load of ''stuff'' to add to his already-stuffed Norsea 27). The design displacement of that boat was, as I recall, around 7,000#; it was after all originally marketed as a boat one could trailer, which is one reason why it''s beam is so narrow. How it ends up having twice that displacement is a mystery to me.
I''ve met two cruising couples who did long distances in Norsea 27''s. Wayne Carpenter wrote a book about traveling with his wife, 2 daughters and a mother-in-law and sailing around parts of the Atlantic (an Amazon search will turn it up), an episodic adventure that struck me as much more fun to read about than participate in. We met the second couple in Horta last summer. Like GUENEVERE in the URL listed above, the boat was heavily (an apt modifier, I think) equipped, had been out cruising for some years, and perhaps contained as many different systems, anchors & rodes, safety gear, electronic gizmos, multiple self-steering systems et al. as any boat which had made it into Faial. Just the canvas ''components'' were gawk-worthy: dodger, bimini, lee clothes, side enclosures, aft enclosure, (plus cabin awning) AND some way to a) rig it all while b) being able to move about and sail...all on a 27'' boat.
If you were to look at each ''piece'' of the owners'' approach, it appeared thoughtful and seamanlike. As I stepped back and looked at the forest rather than the trees, I had to wonder what they were thinking. Perhaps they loved the boat and, incrementally, kept adding things while enjoying their cruising. My hunch is that it was a somewhat different circumstance: they started out thinking a small boat was preferred (shift with background music to Pardey''s mantra, here) but weren''t really willing to cruise or live simply, and so fell into the trap of associating ''things'' with ''outcomes'' (safety, comfort, etc.). Having done extended cruising with a small family (3 of us) on both 20'' and 27'' sloops, I think I can picture what a huge compromise they were experiencing while thinking they were impressively set up.
I digress. I think you could be much more comfortable on a considerably faster boat (once it''s loaded down for the Pacific) that could manage the load-carrying needs you''ll face while spending less than most Norsea 27 sellers seem to think is warranted for their boats. OTOH you won''t own a character boat and you''ll invest significant sweat equity - a good thing as you''ll know the boat well.
If KISS is what you''re after, don''t think that bigger means more complex. As just one eample, when we sailed out of Santa Barbara, a very sought after Pacific voyager was an older Islander 34. Very seaworthy hull with modest, productive lines, usually very few systems, and it dealt well with being loaded out for cruising. They remain cheap, have simple structural components that can be easily surveyed and, if repowered, rerigged, and given good sails and a vane, would be suitable for the same kind of cruising today. (On the East Coast, a common preference for similar use was a Pearson Vanguard). While these are older examples (tho'' not much moreso than a Nor''sea 27) and may be far from the best compromise choice you could make today, such boats by contrast illustrate the characterture-like nature (IMO) of duded-up, high-end pocket cruisers.