Siding is a drainage plane, not a seal
This is the single most misunderstood thing about a wall, and it explains most bad siding work. Siding is not waterproof and was never meant to be. It is a rain screen: it takes the direct hit of wind-driven rain, sheds the overwhelming majority of it, and accepts that some water will get behind it. What keeps the wall dry is the layer underneath — the water-resistive barrier — plus a path for the water that gets past the siding to drain back out at the bottom.
That is why sealing every lap and every gap with caulk makes a wall worse rather than better. A caulked-shut wall still admits water at the top and around openings, and now that water has nowhere to leave. It sits against sheathing and framing. Vinyl siding is deliberately hung loose on its nails and deliberately left open at the bottom of each course for exactly this reason. Understanding what is supposed to be sealed and what is supposed to drain is most of the craft.
