Hard to say. Eventually, it'll get harder and harder to start to the point where you won't be able to start it because it either doesn't have enough compression or because it oil fouls the plug instantly. However, I'd still take it apart and rebuild it rather than wait for it to die, as metal fatigue has taken its toll on the piston and rod by this point as well...you don't want the piston or rod to break and put a window in the block. Then you're really in trouble. If it starts knocking, then it's definitely time for a rebuild. Connecting rod failure isn't far away at that point.
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