Rigging Inspection: Winches used for Standing Rigging

Moving up the mast to the winches: These winches can be considered part of the standing rigging.  What this means is that a winch that holds a cable furling system or a flying jib can also stand all season long or longer without inspection.  It may be a hassle to drop the system but it should be done at least twice a year.
Don't forget that the winch is a vital part of the standing rigging.  The system should be inspected for wear and tear, corrosion, frayed wire/rope and most importantly the fasteners holding the winch to the mast.  If the halyard is wire/rope spliced, be sure to inspect the splice very carefully and the cable for frays.  Inspect any cleats that are used to cleat the tail of this halyard.  Some modern sailboats use line clutches or line stoppers to hold this line fast.  Close inspection of these stoppers or line clutches is standard.  Check for wear and tear, corrosion and proper operation.
Remove the winch head and be sure the winch is well lubricated and the gears are clean. Clean and re-grease if necessary making sure the winch operates freely.  Make sure not to lose the small springs or clutch dogs overboard.  I am speaking from personal experience, this makes for a bad day.

Rigging Inspection: Standing vs. Running

The difference between standing and running rigging can be confusing. Standing rigging usually means fixed wire or cable and even rod rigging that is adjustable by way of turn screws (turn buckles) or dead eye and lanyard on older style boats.  Running is easily adjusted by way of block and tackle, winches and line.  Quite often one may overlook the combination between standing and running rigging for instance a roller furling jib that is hoisted by wire to a winch and left as standing rigging.  Here is where it gets confusing.  Although jibs, stay sails and even some mainsails are held in place by wire this is very common on modern cruising sailboats.  This rigging should be treated as both types, standing and running.
Early types of jib furls were actually an aluminum extrusion taking place of the wire fore stay.  In this application we would treat this as standing rigging and inspect it accordingly.
With even earlier types of furl systems the jib or fore sail was actually stitched to the fore stay wire. This would be treated as running rigging and subject to constant inspection because of the nature in which it operates.  This type of furling is subject to heavy loads and tremendous twisting stresses.  The more modern furling systems consist of extrusions, bearings, roller drums and in most cases the furling drum conceals the turn buckle, toggle, tangs and pins.
Whenever the drum and housing conceal the turn buckle, etc. you may find the original compression wire terminal fitting still in place.  This should be considered suspect and should be replaced as soon as possible with a Norseman or Sta-lock type fitting.  One should also consider at this time replacing the fore stay wire due to its age.
Consult your insurance company in order to meet their criteria and limits on age of standing rigging (10 years is common).