Based on some surveys of utilities I've seen, there are a lot of differing ideas on what the correct amount of breaker maintenance is. However -
First and foremost, of course start with the manufacturer's recommendations; we vary from them as time goes on and experience with individual types is gained. The specifics obviously change for the different manufacturers & models of breakers. Depending on the type of operator used (spring, air, hydraulic, etc) the maintenance required can change significantly.
But as a rough summary - monthly patrol checks (record counters, , check gauges, stick head in cabinet as a quick observational check); annual heater and operational checks along with a basic operator inspection (it's cold up here, heaters are important); 5 year checks on density monitors and depending on the operator other pressure switches, etc; and usually around 10 years, major maintenance - usually a major mechanism check (including lubrication), breaker timing and motion analysis, insulation checks (esp at those higher voltages as grading caps are more likely), gas checks/density monitor checks, etc.