The difficulty of removing older nails from wood increases due to several factors, including chemical changes in the wood and rust accumulation on the nails. Over time, wood fibers can expand and contract, creating a tight fit around the nail, while hardened pine resin can act like glue, further securing the nail in place. Rust on the nail can create barbs that complicate removal, and the abrasive nature of rust can damage the surrounding wood. Seasonal moisture also contributes to rusting, making nails even harder to extract. Overall, the combination of these factors leads to a significantly more challenging removal process for older nails.