Catalina 42 for Blue Water?
Brad, I''d like to echo Jeff''s observations except that I''m a little (that''s "a little") less worried about the charter side of your plan and a lot more concerned about the blue water/extended offshore sailing side. A circumnavigation puts wear on a boat that isn''t just ''decades of coastal cruising'' but is uniquely and extraordinarily harsh in its own right. As just one example (and there are others), which route are you planning for your circle: Red Sea or Cape of Good Hope? Either choice will present something well beyond coastal cruising, for an extended period, and that''s after a 3,000 mile rumble in tough tho'' fair winds across the Indian Ocean.
OTOH I''ve been especially impressed - perhaps ''amazed'' is a better word - with the Copeland''s experience sailing their (early 90''s, I believe) Beneteau. They''ve circled, done a subsequent circle around N/Central America W to E, and then put the boat thru a real bashing by sailing her too early in the season across the N Atlantic to the Med. Yet the boat has handled all this well, not that Liza nor her sailing/racing husband are slouches at knowing when to push the boat and when to protect her. This doesn''t mean I think buying a Beneteau is a grand idea, but to me this is evidence that shopping by brand name alone can be misleading, whether one is ''pro'' or ''con'' WRT a given brand.
Another wrinkle is the spotty quality of these production boats. I personally know of one Catalina (a 40, as I recall) where the rudder could not be turned under certain points of sail. The cause was that the hull flexed so extremely (we''re talking in Charleston Harbor''s open bay) that it fouled the quadrant. The boat was toast, and was quietly recalled by the factory (to be ''fixed'' and then resold, of course). How you reconcile your desire for long-term structural health with the history of these boats - no survey is perfect, nor does it offer a guarantee - I don''t know. (Just to be fair, I''ll add that a Hinckley 60 we came to be quite familiar with in the Caribbean had a massive hull failure when only a few years old, again due to shoddy build practices on a cored hull).
One suggestion: review the recommended characteristics discussed in John Neal''s website, along with the many boat brands on which he comments. John is about to complete 400,000 ocean sailing miles; his experience is unique and he''s a fair, thoughtful fellow. And then shop by basic build & design characteristics rather than first by brand; this is harder but gets you closer to your goal. You''ll find his site at www.mahina.com.