One reason for not inspecting … Reliability breeds complacency. I think that I am more like Will in that I don't do a conscious walk around every time I sail. One reason is that in 50+ years of boating (I'll have to admit that I have never been an intensive sailor), I've never experienced a catastrophic failure. I think that I am generally aware of the condition of the fittings and wires. I know that I have never seen a fish hook on a shroud or anything that looks suspicious and I know that I would never even consider sailing the boat if I were to suspect anything wrong. I replaced all the standing rigging and fittings just 2 years ago, not because anything looked even slightly damaged or deteriorated, but because I only knew the age of the forestay, which I replaced soon after purchasing the boat 14 years ago (the swaged fitting was slightly bent as noted in the survey). I did not know the age of the other shrouds.
Now that I know that standing rigging is new, complacency is easy. But this thread has made me consider that I should at least do a careful check of all the cotter pins, since I didn't step the mast this spring and I had noticed a few on deck and dismissed the notion that they came from a fitting (generally because they looked like the ones that would have been removed last winter).