Mini-rant, so I apologize in advance. I once threw an anchor over with no rope attached. There, I've admitted an ounce of stupidity myself.
I'm glad I spent 8 years sailing my Prindle beach catamaran; I learned more about boat handling under sail than I will ever learn with a larger boat, because I could take her to the edge of the envelope and beyond. I capsized her and got beaten and destroyed by thunderstorms, and learned some humility. I'm glad I sailed my Stiletto for 16 years; I learned to balance attentive boat handling with navigation and cruising. I was never beaten and destroyed by any situation, because I had learned those lessons. I never placed myself in situations I couldn't manage. With my PDQ, it is more about learning systems than sailing. The boat is rock solid, and unless I seek out gale conditions or throw all of the sea sense I've gained to the wind, I can't imagine real trouble or challenge on the Chesapeake or coastal waters, not like the Prindle threw at me on every breezy day.
It's common to read a post on a forum or blog relating an adventure or misadventure born of inexperience or limited understanding of sails and boat handling under sail. Good folks sharing their foibles for the benefit of others. I've made all of the mistakes; I simply had the good fortune to make them on a beach cat, years ago. Would an apprenticeship in small boats help all would-be cruisers?
There are some tips to ease the problem, if you get caught. Turn down wind to blanket the jib, then either lower or furl. If roller furling, DO NOT let the sheet fly in strong (over 20 knots true) winds or something will get tangled in something. As for the main, can you make the turn to windward if you let the sheet and traveler ALL the way out? If not, try pulling the main down by rigging a line between the mast and the slugs and using that to pull it down. Try placing a hook in the grommets and using a winch to pull it down. Then swear NEVER to make the mistake again.
It is common to loose rudder control when over powered off the wind and round-up. This should NEVER be a surprise. If you feel the stern starting to rise or see the bow starting "swim" (as cat sailors say), back off. The sailors in the above image should have had time to bear off or blow the sheet; clearly, they didn't manage because they were over pressed... and I bet they considered it a surprise.
* Engine fails in storm and can't deal with sailing in rough weather. Dingy sailors ALWAYS learn to sail in a gale, because a small craft advisory is a gale to them. Every sailor should know how to push the boat to the limit with each set of sails, and be prepared for the odd handling characteristics of boats that are over-pressed. It's too hard to explain in simple words; it's a seat of the pants thing you learn from sailing a dingy in too damn much wind with sails feathering and making leeway and not being able to tack or jibe in any normal manner.
* Towed into port because the engine failed. Dingies don't have engines and so you learn to plan your entry into a harbor. You can sail anywhere but into a very trick slip, and you can surely sail close enough that your tender can push you in. This is the way it was done, in years past - "lower the long boats and start pulling, men." I've had 4 engine failures in 17 years of having engines, and none were that hard to work through. I would be embarrassed to be towed, if I had the ready means to deal with it. It would prove to all that I had failed a basic test of seamanship.
On a bigger boat like the PDQ, this takes teamwork and planning. Discuss the options and the plan while outside: when each sail will be dropped, how each turn will be made, and what to do if something turns out different than you expected (windshift, tide). In general, use the jib for the close approach (it can be let fly or furled) and the anchor should be unlocked and tipped. If it looks hard, you did something wrong. More planning.
I'm embarrassed to admit I've had towing insurance, just this year and last. The first year I got it over night on my delivery trip, as I realized I had one engine out and one I didn't trust. The second engine did fail, but we sailed her in to the slip. We also grounded a few times but had no troubles getting off. This year... well buying the insurance was a mistake I feel guilty about. Wish I could get a refund. Never again.
The Stiletto is a fast but tender boat; he got distracted, and the mainsheet was out of reach.
* Steering in big waves. A dingy sailor finds it instinctive and relaxing. They also know when to get scared. I used to launch my cat off the beach; handy lessons to have had when I first met breaking inlets in a bigger boat. I knew what I could do, and what I couldn't do.
* Disorientation at night and in the fog. I've seen sailors that could only maintain course with eyes locked upon the compass or the tell tales. The GPS and wind instruments mesmerize them. They develop no real sense of the wind and waves once they lost landmarks and vision. To a small boat sailor, a continuous awareness of the wind direction and strength, and the wave direction and type, is natural. They don't think of it, they are simply instantly and continuously aware of their surroundings.
* Sailing without electronics. Although they have their place, in general I hate electronics. They keep a beginning sailor's head in the cockpit, instead of watching the water. I actually threw a towel over the instruments on my sail home, for the first hour. To much information, when what I needed to learn was her balance.
Piloting too. You can't really learn piloting when there is GPS to fall back on, or at least it takes longer for it to become easy, comfortable, and automatic. Piloting with the senses make the sailor look at he color of the water, the shape of the waves, the steepness of headlands, and the importance of staying oriented. I have lost GPS twice, both when out of sight of land. Neither occasion resulted in disorientation, because I was not depending on it. I was keeping a running log.
* Sealegs. If you can get comfortable walking around in a dingy or on a beach cat, you've got it down. You learn to settle low with a lurch or lean, not to fight it.
Some fear small boats, I guess. Some find them undignified. Some believe they are toys. What shame; they buy a big boat without the traditional apprenticeship, they spend years getting comfortable sailing in a breeze, perhaps never learn the danger signs when the boat is pressed too hard, and perhaps never learn how to press the boat hard and efficiently when there is a lee shore looming. I would love to have a place to keep my old cat on the beach, ready to go. I haven't outgrown it.
As I said at the beginning of this post, I have learned a lot from bigger boats: systems, trip planning, team work, anchoring, systems, handling with twin screws, more about systems, and relaxing after a good day in more comfort. But I learned everything I really needed to know about sailing from the beach catamaran. Those years have given me confidence and a feel for the weather that I would never have gained with larger boats.