We ordered a 'rigging inspection' from Torreson this year when we had our boat hauled. Wanted to get ahead of potential problems before they became 'problems while underway'. They recommended the following repairs:
The wooden spreaders were showing signs of age, and they suggested either replacing them with new wooden ones or new aluminum spreaders, and while we were at it, replace the spreader lights and check the wiring up the mast. We'd noticed that the port spreader light looked like it was damaged, sometime over the past winter (likely when the marina took the mast down to do last winter's repairs) and none of the mast lights worked this past summer (although it wasn't a pressing issue, since we didn't use them at all). We decided this would be one of the first of the repairs we would address over the winter.
Winches need to be serviced. We knew this was an issue, as we'd noticed that the starboard one would scream loudly under certain conditions, this will probably also get addressed this winter.
Lifelines were inspected and the lower ones seem to be ok, but they recommend larger diameter lifelines on the upper position. Maybe. Maybe next year.
Halyards need to be replaced, as they are showing their age. Was hoping to put this off another year if possible, but if we can afford it, perhaps we'll do this over the winter as well. I think we are also going to need to replace the docking lines and a few jib sheets this coming year. All are starting to show signs of wear, and I get nervous every time a stiff breeze blows up, wondering if the boat has snapped her dock lines.
We haven't got a bill yet for putting the canvas cover on the boat. I'm a bit anxious, wondering when they plan on doing this, as snow keeps getting predicted. We called to ask about it, and they assured us that we are still scheduled to have that done. To be honest I feel a lot better doing these things ourselves, but free time keeps coming at a premium these days.