Some would have you believe that anchoring in the old days was a harrowing experience due to the lack of reliable anchors and gear, but that was not the case. Sure, we had different equipment and systems, but we also used it differently and I really don't think we had any more problems than today's cruisers at anchor--in fact, I'm pretty sure there were less issues. The reason? People had to learn the craft and did so because they didn't have push-button windlasses that allow huge, heavy anchors and chain. Without a windlass even boats up to and beyond 40 feet usually relied on muscle power to handle everything, and that often meant a short length of chain, mostly nylon rode, and something like a 20-35-pound Danforth anchor on the end. Having to lower this by hand meant that someone was up on the foredeck carefully lowering the thing over the side, feeling when it touched bottom, and then gradually easing out rode, snubbing the anchor periodically as the boat drifted back. Then, because we didn't have all-chain rode we put out 5:1 or 7:1 scope, checked that the anchor was really well dug in by backing down while feeling the rode and watching, and anyway a Danforth beats any modern anchor for sheer holding power in a straight line according to almost every anchor test ever done.
In short, better technique meant that we used what gear we had to the fullest instead of relying on some miracle design to just work. But, but, what did we do when the wind shifted? We often used two anchors in a Bahamian moor, as was taught by Robert Danforth Ogg in the little booklet that generations of boaters got when they bought their anchors. Pick up a copy of Anchors and Anchoring by R.D. Ogg if you ever find one. There were many generations of this booklet published, but they still provide some of the best basic anchoring advice and information ever published. Plus, Ogg backed up his advice with what is probably the most extensive testing program any anchor design has ever gone through because of the original requirement to create an anchor that would allow landing craft to winch themselves off of beaches. Today, an aluminum Fortress anchor does even better, but it is nothing more than a refined version of the original Danforth made of a different material.
How good were these ol' school anchors? We rode out Hurricane Gloria on two Danforths and a CQR set in a star pattern, and sat in one place while most of the mooring field dragged by and went ashore on Long Island. Two Fortress anchors helped hold our boat on a mooring in Cuttyhunk Pond during Hurricane Bob--it took most of a day to dig those anchors back out of the bottom. Short of something breaking there was no possibility of those anchors dragging. When hit by a tornado in the Chesapeake a CQR and a Fortress held our catamaran in wind estimated to be over 100 mph. The force of the wind took one boat's Avon complete with outboard and blew it through the air and up into a tree ashore, where we later found it. Just anecdotes, but to me they have proven that anchoring technique is more important than having the latest and greatest gear.