That is a tough choice...
I owned and loved my classic ketch for the duration, however shortened by Hurricane Sandy... I had bought her for life - it was what pleased all my senses and I thoroughly enjoyed sailing her, not bothered at all by her lack of ability to claw upwind, which was more than made up for by her performance on a broad reach. She had plenty of headroom in the main salon but then it quickly got cramped when moving forward into the head and V-berth area. Everything was warm and wood - mahogany throughout; fully equipped and with lots of storage and generous tankage.
The story was that the PO had her rebuilt for extensive cruising - with reinforced decks, chainplates, propane heat, new sails, electric hot and cold water, shower, etc., etc.
He, however, soon realized that with all the work done and the love he had for her, she remained what she was - beautiful with all her charm but also a compromise with her shortcomings. My understanding is he attempted to cruise her but soon realized that not only he needed a lot more room, but also that this new lifestile would be too harsh on her. The wooden masts, booms and blocks needed frequent care; her painted hull needed frequent cleaning and polishing; the plywood decks were vulnerable to water intrusion through the many penetrations and thus were exposed to rot; the exposure to the elements - brutal UV, constant salt spray, continuous motion, started to quickly show their effects, take their toll and he ended up coming home and selling her to someone that would put her back in a lifestile, a reliable and constant cycle of care, that would preserve her rather than tear her to pieces.
From my part, now that she's gone, I too had to make a decision - there were several other classic ketches on the market that were priced right and easily would have filled the void I experienced (and maybe would have put a bandaid on the guilt I felt over having placed her in the path of Sandy and then left her vulnerable on land, where she could not rely on her robust build, her excellent seaworthiness to fight for her life, but rather, surrounded by lesser vessels was pushed, rammed and shoved into submission and ended up - albeit intact yet, on the pile with all the others).
I slowly went from love and lust to reason - learned by knowing what it took to own, maintain such a vessel and decided on a more roomy, more airy, less maintenance design, which I hope will please me with different rewards... I haven't sailed her yet, but I am looking forward to bringing her home from Providence, RI and, more importantly, this time my wife is too