Long time lurker here, I have gained a ton of great knowledge from this forum over the years. I sold my San Juan 21 four years ago and bought a 26M (wanted something bigger to say overnight, etc), which I had wanted to own for many years. Now in my fourth season, I have made probably every possible mistake and have learned it's quirks! my wife and I had a ton of fun with the boat. However, I still miss the sailing capabilities of my San Juan. As a result, I have researched the possible alternatives (true sailboats) in the 26' range but when I look at the boats in the same price range as my 26M, they are dated and there are so many maintenance items (decks, keels, older sails, limited trailering, etc). And to top it all off...I feel a sense of betrayal to my 26M LOL. It doesn't feel right

So my question is....have you ever looked at moving back to a true sailboat, and if you did, were there regrets? And what particular model did you end up buying?
Thanks