If your oxygen system isn't holding oxygen, then obviously it needs to be fixed. Perhaps I missed something, but I think you just asked if when a system is found to be malfunctioning, should you ignore it, or fix it. Is this so? Of course you fix it.
If the system is bleeding down, the source of the leak must be located and the problem solved, period. A bottle should never leak. If the bottle is leaking, you have a major problem and definitely should not fill the system or put it under pressure. Leaks occur at joints and fittings, and at the mask.
Gas pressure lines leak the gas under pressure around threaded fittings, cracks in lines, at the mask. If a soap solution is sprayed onto each potential leak site, bubbles will form where the gas leaks. What type of soloution depends on the gas. In this case, oxygen. You can't use any soloution with a petroleum base, because it reacts with with the oxygen. While some mechanics will use a dishsoap solution, a special solution is sold just for use with oxygen systems which doesn't leave a deposit, doesn't attract dirt or contaminants, and doesn't react with oxygen.
Finding and fixing the leak isn't preventative mx, especially with an oxygen system. Simple mistakes like improper use of sealant tapes or compounds can cause big problems in the oxygen system, to say nothing of improper torque on fittings, line flarings, etc.
Fix it.