I put a few squirts of grease and gear oil in mine since this is the first time I have ever used it. I will take everything apart this summer to clean all the old grease out. It doesn't take very long to take everything apart. It's really a very simple machine.
If you put grease on your drill bits and tap very few shavings will get inside. Even if a few did get in, it's not a hydraulic system in there. I would say to be on the safe side take the boxes apart at least every 10 years or so and clean and repack.
Edit: To check the level stick a zip tie in, if it comes out dry, add lube.
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Travis
1993 Cub Cadet 2064
1988 Cub Cadet 2072
1980 IH Cub Cadet 782 w/CH20
1966 IH Cub Cadet 102 w/K301
1961 IH Cub Cadet O
1967 IH Cub Cadet 102 & 122
JD 2155 w/ 175 loader
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