There’s a moment every cruiser hits, usually somewhere between the spreadsheet and the dock walk, when the question stops being “new or used?” and turns into “what kind of trouble do I want, and when do I want it?” I’ve seen plenty of shiny boats humbled by a loose wire, and plenty of older hulls run steady as a metronome because someone cared for the unglamorous bits.
Age doesn’t tell you much by itself. What matters is whether the boat’s been built and kept in a way that matches how you’ll actually use her: long spells away from help, heavy loads aboard, and the sort of small failures that show up at sea instead of at the slip.
Pick the path that leaves you with confidence in the rig, the steering, the engine, and your ability to fix what breaks. Everything else is just brightwork.