I have rarely heard of anyone 'ending up in trouble' purely because they did not have the most up-to-date chart.
If you carry several hundred charts, as we do, its a council of perfection to expect them to be all up-to-date. A chart of the correct scale say 5 years old is quite acceptable in most (though not all) circumstances.
Indeed, the charts themselves are much older than you think. Look at the survey and publication dates of new charts - often 25 years old even round Britain. Subsequent corrections cover navigation marks, harbour workings and major wrecks, but rarely changes to the underwater topography or landmarks. The Admiralty charts I recently bought of the Bahamas were actually 150 years old, in an area of high coral growth! And the buoyage and shoremarks hadn't been changed since a hurricane took most of them out 5 years previously.
Even with brand new charts, it makes sense to cross-check any crucial lights or buoys against all other sources to hand, for example from the Almanac, or from up to date small-scale charts.
Charts, like everything else, are just AIDS to navigation, and should always be used with caution. You just need more caution with older charts.