Some quick math. Suppose it turns 1200 RPM, rated. That's 20 rev./sec., or 50msec/rev., or 25msec/stroke. It'd still run well enough if you lost 10% of total cylinder pressure in the last half of the compress stroke and the the first half of the power stroke (25ms total).
Going on some very old, very fuzzy memories, if you lose 10% of total pressure in one second, you probably want to do the rings and valves. Or if, cranking by starter, you only reach 90% of expected PSI, freshen the engine. Some of those old engines will run for years with one end of the head torqued finger tight and a couple broken valve springs.
As long as the engine starts easy, sounds smooth, feels smooth, gives acceptable torque, the top end sounds quiet, and a borescope reveals nothing alarming in the cylinders, the motor's good to go for moderate duty.
In human terms, you aren't good to go full bore 18 hours a day any more. That old motor likely isn't either. At ½ duty, it might just run another 20 years as-is.
If you're taking the tracks apart to clean and lube, you should consider a lube that resists pound-out. Amsoil makes a good one.