I assume at that point the onus is on the cruiser to wade through years if not decades of Notice to Mariners to update every chart, which is some cases is going to mean moving four buoys and tracing in a new TraveLift slip, but in others could mean hours of careful calligraphy and a stock of very fine-tipped pens.
Not to mention that some older charts are off due to Capt. Cook's intestinal gas during the noonsight in 1773 or some other cumulative effect.
I think sometimes it would be prudent to figure out the last year in which a chart was updated, just to avoid such mistakes and to have a degree of confidence that the datum isn't obscure, or, like using a 20 year old chart of Dubai, that there haven't been "developments" that constitute an entirely new coastline.
I use a variety of old and new charts for Lake Ontario, which changes little in terms of reefs or things that are going to tear me a new thruhull, but which alters greatly in terms of buoyage (often the important stuff that does mark those few awash rocks and the like). Notices to mariner updates are a very good idea if you are travelling at night without RADAR. By day, a chartbook and the Sailing Directions and a large-scale chart to plot bearings suffices.
Approaching a South Pacific atoll with a hand-drawn map in a book by a guy named "Coconut Charlie" who says "last time I was here they were blowing a hole for a new hotel and the spoil field might be here"...I'm going to want the new chart!