With a 29 you should be able to go aloft, or careen the boat, or pull alongside something so you can eyeball the masthead without pulling the mast. You can inspect the shrouds with an eyeball, some binocs, and a rag. Wrap the rag around each shroud, use an uphaul+downhaul to haul it up and down. If there are no meathooks, no catches, it is probably pefectly good. One meathook is enough to condemn the wire though.
Same thing for wear aloft at the spreaders and other points--you should be able to get a close enough look without pulling the stick, unless there's been something extreme to concern you. 20 years, sure, replace away. But at ten with moderate use? Nah. Find a rigger who doesn't drive a fancy car or serve caviar to the customers.