https://www.quora.com/Whats-the-largest-sailboat-a-person-can-safely-handle-singlehanded
This fellow does a great job of explaining the issues in single-handed sailing.
Chris Price, I like sailing on and working on sailing cruisers.
Updated September 29, 2018
Kevin’s answer, Kevin Cooke’s answer to What’s the largest sailboat a person can safely handle singlehanded?, is the benchmark for this question.
This is one of my pet peeves. If something goes wrong and all lines lead aft it makes it worse.
For short-handed sailing – which means singlehanding some of the time as one crew will be off-watch – it is often a good idea to lead the major control lines back aft to the cockpit. Most people aren’t all that active or strong, and many sailboat crews are getting on in years. It saves effort, saves going out on deck in wet or rough weather, and therefore improves safety.
The problem is that when anything bad happens, you have to fix it at the mast. Sometimes on the foredeck. At these times the lines need to be 100% optimised for at-mast handling, or the situation will have been made worse for solving a serious problem that will inevitably occur at the worst possible time.
This is what happened to him. Read the full story on the link above it is a great read.
OK let’s drop the chute then. It won’t be easy because you’ll have to gather in about 3 acres of unruly nylon in a rising wind. Singlehanded. Luckily you have a great windvane steering the boat, so no worries there (maybe a Hydrovane or a Monitor). So we let off the spinnaker halyard carefully, and prepare to let the chute’s sheet fly and bag it. Simples.
Only nothing happens. The halyard is jammed at the masthead. The wind is still gradually increasing, and so are the wave heights. They are only tiny little miniature waves so far, just ripples (15 feet – you’ve seen much, much bigger) but they’re growing.
What to do, what to do? Leave the sail up and you will reach supersonic speed, which is not good in a small boat – something will break and it could be serious. Cut the halyard? No use, it’s jammed solid up top. Let fly the sheet and tack, and let the sail fly out free ahead from the masthead? Hmm, well I’ve had that happen before by mistake and it felt like the mast was going to come down any minute with all the banging and crashing and shaking. That’s a no-go too.
Only one option left: climb the mast.