Good topic!
The causes of dimastings are as varied as the rigging of boats.On a race boat, not getting the runners on during a normal gybe can have the stick out of the boat.Good cruising rigs should stand with any one shroud broken. Excellent cruising rig design allows any two shrouds to fail and the mast remain upright long enough for the crew to react (change tacks etc to relieve stress). For example, on a Catalina 30, the 304 alloy 3/16" lowers are marginal, the mast will probably stand if one breaks. Replacement with 316 alloy lowers in 3/16" puts them over the edge IMO. I like to see 7/32" wire and 304 alloy for those shrouds. Many boats from the 70's were designed with 304 or 302 alloy wire, 316 alloy is 15% weaker and can increase the risk of failure on boats that have minimum safety margins built into the rig.What we are starting to see is wires failing from age. Stainless steel has a finite fatigue limit before it becomes suspect. It can look fine and show no external flaws and fail the next day. A good rule of thumb is to pull the mast and do a detailed inspection every 5 years. Some riggers recommend 1x19 wire be replaced every 5-7 years, particularly 316 alloy. Navtec says rod and wire should get a professional inspection after 40,000 miles. True, there are boats that sail with 30 year old wire and the rigs don't drop, but no one can say that the rigging is sound. Just because the boat is not sailed often does not prevent fatigue stress, a loose rig rolling in the slip with each wake and gust of wind can fatigue the wire just as fast as sailing the boat to Hawaii.Reusing cotter pins is a no-no. Using split rings instead of cotters to secure clevis pins is a no-no. Using mismatched pin and hole sizes is a no-no. A 1/4" wire might have a 3/8", 7/16", or 1/2" pin. Putting a 3/8" pin into a 1/2" chainplate because the turnbuckle toggle will only take a 3/8" pin is asking for trouble. The 3/8" pin in a 1/2" hole is much weaker than the same 3/8" pin in a 3/8" hole. If the chainplates have 3/8" holes 3/8" turnbuckles should be used, if the holes are 1/2", use 1/2" turnbuckles. What is scary is I've seen brand new production boats where the turnbuckles have been downsized but the chainplates still have larger holes. This is on factory supplied rigging! Speaking of turnbuckles, stainless turnbuckles that use stainless rigging screws are automatically suspect. They require yearly inspection (complete removal of the turnbuckle body for cleaning, thread inspection, and lubrication. These are the ones that make the screech of death as the threads gall when you try to adjust them.

Chrome Bronze turnbuckles with stainless rigging screws are fine, the seldom seize or gall. Navtec turnbuckles used to come with SS rigging screws, if you have these, replace the screws with bronze and then replace the rigging screws every 40,000 miles or 10 years.Installing roller furling on a headstay that has no toggle at the masthead can bring the rig down.As mentioned earlier, loose rigs cause more problems than properly tuned rigs.If the rig will not hold it's tune for the sailing season, there is something wrong. The wire is no longer elastic, the chainplates are distorting, the compression post or deck is crushing, the hull is getting soft ... something is wrong.Yes I'm a rigger, I'm not trying to sell things that are not needed. We make more money replacing the whole mast and rigging after it fails than we do just replacing the wire. The insurance companies are starting to take a look at this and rig inspection requirements for insurance surveys will probably get stricter in the next few years. 15-20 year old wire may not be insurable.Once the rig is in good condition and well tuned, roll over and collision are the most common causes of dismastings.