There is a saying among pilots that "a superior pilot uses his superior judgment so he does not have to use his superior skills". The idea is that if you are regularly displaying super flying skills to pull yourself out of dangerous situations, you need to ask yourself why you keep getting into those situations. During a long conversation during our Marquesas passage, we changed the saying to fit sailors:
"A superior sailor uses her superior judgment so she does not have to use her superior skills and she uses uses her superior skills so she does not have to rely on her superior equipment."
The idea is that the first line of defense for keeping yourself and your boat safe should be good judgment. For example, in choosing the time of year to sail a particular ocean, or choosing a weather forecast for departure.
Often, even using good judgment, you will need to use your skills to keep yourself and your boat safe. For example, big squalls hit during a good weather forecast and you have enough observational weather skills to assess the weather on the horizon and reef down the boat.
When you get hit by something despite your judgment, and despite your skills (or in the case of failure at both, particularly while learning), you lean on your equipment. You start muttering to yourself "she's a strong boat, she's a strong boat" or "I'm glad I changed the rigging". For example, you are on a longer passage and a bad weather system overtakes you. You use your storm tactic skills but at the same time start praising Henri Wauquiez for building strong boats.
There is no such thing as risk free ocean voyaging. Actually, there is no such thing as risk free living. Even when we were commuting to work and living in a house we accepted the risk of driving on a freeway, the risk of forest fires, the risk of crazy violent people in our neighborhood. We all try to minimize our risk but we all choose a level of risk that we are comfortable with.
We have seen a lot of lightly built boats in the South Pacific. Every boat owner has to decide how much they want to have the strength of the boat backing their judgment and skills. It is quite a personal decision, cultural too in our experience, which depends on a lot of things including your own level of comfort with risk. We believe that with enough good judgment and skills, you can sail most boats across oceans by sailing them within their level of strength, as long as you are comfortable with the presumed risk. This combination is, we believe, how good captains can deliver lightly built boats across oceans. Of course, we feel more comfortable in a strong boat, but we chose a fin keel over a full keel despite the opinions propagated by desk cruisers on sailing forums. People say that you should have a full keel boat in case you hit a reef or hit a submerged container. We decided to work on our not-hitting-reef skills, to accept the risk of submerged containers (and carry a life raft), in order to have the fun of a boat that sails well in light air and points high.
Sometimes acceptance of risk means increased fun – that is the logic behind leaving our couches to go cruising, right?
If you look at this saying another way, it might be more important to prepare to go cruising by working on your judgment (learning about weather, learning what conditions your boat feels comfortable in so you know which to choose), and by working on your skills (what is your procedure for reefing your main downwind in big swells) than working on your boat.