Furling Main Sails
You are not old fashioned. In talking to experienced delivery skippers who have spent much time offshore with mainsail furlers, they tell me that it is only a matter of time until a jamb occurs when reefed. I think that Jack and I have said the same thing but from a different angle. The type of people who generally buy a mainsail furling system are less concerned with performance that ''push button'' sailing, and for those people, they love the in mast furling until the first time it jambs and they can''t clear it. I have generally understood that the Selden is a better set up than some of the other furling systems, but one of the most harrowing stories that I heard was a Trinitella with a Selden.
As to the so-called Brewer 12.8 "cutter ketch", first of all, there is no such thing as a "cutter ketch" or a ketch rigged Brewer 12.8. You are looking a ketch with multiple headsails and what distinquishes a Brewer 12.8 from a Whitby 42 is that the Brewers have a cutter rig (vs the ketch rig on the Whitbys) and the Brewers have a Keel/centerboard (although some of the last Whitbys have a fixed keel.) The Whibys were a significantly less expensive boat and so you see a lot of the later Whitby 42''s advertised as Brewer 12.8''s.
The Brewer 12.8''s (cutters) are very good sailing boats. My father has one and I have been very impressed with how well his sails. (By the way,Dad''s boat which has slab reefing and a dutchman system is for sale in Sarasota, Florida. He does not have it listed so you would need to call him directly at 941 371 0659 or email me for a listing) The cutter rig on the Brewer 12.8''s have an ingenious rig that allows the staysail to be quickly and easily relocated to the base of the mast so that the boat can be normally sailed as a sloop but with the staysail ready to go at any time. Set up as a sloop is a very much easier way to sail any cutter when you need to tack a lot and so helps make the boat an excellent coastal cruiser as well as an offshore boat.
The ketch rigged versions of the so-called ''Brewers'', fall heavily into the "crab crusher" category in terms of sailing ability. The added loss of performance involved with a mainsail furling system would only push it further into the realm of crab crusherdom. we each determine what is an acceptable level of perforance for our tastes and needs, and there is a wide range of ''acceptable'' sailing performance out there. But a Whitby 42 with an in-mast furling system, would fall heavily into the bottom of a performance range for anyone who cares about performance.
With all due respect, the Brewer 12.8''s (in other words the Cutter rigged K/B boats) were conceived to be just what you are looking for, an offshore capable distance cruiser that can be handled by an older couple. The genuine 12.8''s all came with very heavy duty hardware and electric primary winches that can also be used to haul up the mainsail, taking away the usual primary arguement for having a furling mainsail.
I guess in the end it comes down to what you can live with. As Jack says, for some, a furling mainsail is an acceptable risk. Having listened to a few more stories of failures than Jack has encountered and with the greatly reduced lifespan of a furling mainsail, I would consider a mainsail furler system a ''deal breaker'' but that may just be my opinion.