With all due respect, while the Swan 44 is a very nice boat and a real classic, I would think that their 7''-6" draft would make them pretty ill suited as a circumnavigator if the trip around includes such areas as the Bahamas or the Pacific atols.
I also disagree with your statement That the Swan 44 was designed "prior to all the rule cheating goofyness of the IOR era" These are quintessential early IOR boats with all of the "cheating goofyness of the IOR era" as an integral part of the design including pinched ends, huge headsails and small mainsail, and enough tumble-home to assure that you will roll the rudder up out of the water on a knockdown and roll like a son of gun downwind.
Given Jeff''s budget, if he is going the Sparkman and Stevens early IOR boat route, he would be far ahead to try to find an early 1970''s era Tartan 41 which were equally ruggedly built, lacked a lot of the high maintenance fru-fru (such as teak decks) found on the Swan 44.
Please don''t get me wrong here. The Swan 44''s are really neat boats, but IMHO they are really not in line
with Jeff''s goals.