Consider the ability to work the Bayfield into a favorable trade for a larger boat. Many parties are interested in moving down in size/complexity. Good luck.
One of my buddies here at the Nyack Boat Club ( Hudson River in NY) just completed a 2 year stripped out total restoration of a Cape Dory 28. He's a great mechanic and a master carpenter. He pulled out everything including the engine, interior, mast, plumbing, cabinets, chainplates etc. He then proceeded to go over the hull interior and exterior. Then faired and painted (polyuth) interior and out. Next he replaced all portlights with metal ones. Then replaced all teak exterior trim with new teak. Then he replaced the main interior bulkhead and chain plates. Then the rest of the interior pieces were re assembled. Anything so so was replaced. Anyway the boat looks new, maybe better. And I would take this one to Bermuda without any hesitation. Now he latched on to a 32 so he's going to do this all over again!! A glutton for punishment. Im sure the 28 will go up for sale this spring, but he'll ask around 20K+We have two boats, at both ends of your length spectrum. Both are great boats for their length, and we love them both.
There is a HUGE difference in operational costs on a 34 footer vs a 27 footer. Sails, bottom paint, slip fees, etc. And as other note, the systems are much more complex. Not trying to talk you out of it, but remember that when looking at costs beyond the purchase price.
A C&C 29 MkII is a very nice boat if you can find one in good shape.