One difference between sailboats and power boats is the rigging. There can be a fair amount of expense in righting deficiencies of the rigging. To begin you have to make sure all the rigging parts are there. If the rigging is off the boat it can be a challenge to put your eyes on each component. Sometimes they are stored away from the hull but it is worth the time to uncoil the standing rigging, inspect the mast and boom, make damn sure the gooseneck connection is complete and not excessively worn (They can be very difficult to replace).
So for standing rigging look for broken wires, areas unwinding of the wire and kinks. All are bad. This basically a pass/fail test. Some advise dragging a cloth over the wire to find broken strands. Also look at the turnbuckles to assure that they aren't bent and take pictures of the position of the turnbuckle on the studs. They shouldn't be at any extreme. If the turnbuckle is at its extreme end, or close to it, the boat hull or deck could have deficiencies.
For the mast inspect for any dents or any signs that it is not straight. Also look at the masthead - take pictures - for the condition, material and shape of the sheaves. And look at the spreaders paying attention to how they are attached to the mast and the condition of that attachment. And inspect the spreader ends where the shrouds attach. At the base of the mast look for wear or damage on the base or hinge. Also inspect any hardware that passes a line from inside the mast to outside including halyard boxes.
For the boom inspect the endplates (Boom side of the gooseneck) and the end of the boom. How are they attached? Aluminum rivets, SS rivets, machine screws? What is the condition of the fasteners? There should be no play in the hardware. If lines exit the end of the boom. take pictures. Inspect the mainsheet and vang attachments. Again for hardware condition and for those highly loaded areas any elongation of the holes in the boom suggesting excessive wear. Look at and try to understand the reefing system (You may end up changing it to your liking) and outhaul.
There's probably a lot more and other posters can fill in what I've missed.
A sailboat is not a power boat with a mast. When a sailboat loses its rig insurance companies generally total the boat. Imaging the expense of shipping a mast. Without good rigging a sailboat is a very poor power boat.
