We clean the bottom every Spring, whether it needs it or not! The main is only a couple of years old, nothing high-tech, but not blown out. The jib was old when we bought her, 8 years ago. Doyle says it servicable, but the leech and foot were built to be sacrificial and need to be replaced.
I had a barber hauler on my Prindle 16' beach cat and thought about the idea of pulling the jib sheet in with such an arrangement. As things stand now, I don't think the jib would clear the spreader, but I need to get the jib recut this off-season and I could specify that. It would result in a smaller sail, and the PO said she came to life when he put the 160 on. I don't know what the sail was that he replaced, possibly a 135. Based on what he told me, I wouldn't want to go too small.
In light air, I pull the traveller to windward to keep the boom centered and always thought I benefited from that. But recent racing has shown that we drop back when I do, and keep better pace with the traveller centered. This has been in the 9 - 10 kt range. Maybe in 7 - 8 kts, I benefit from the windward position, but I'll have to try that in a race to really see.