Does an ingrown toenail that has been ingrown for years then finally removed more painful than one that has occurred recently and removed?

Not usually: Whether this is an acute or chronic condition, you can get good longterm relief by visiting a podiatrist. Ingrown nail surgeries are a routine procedure for most. If you have diabetes, circulatory issues, healing issues or a longterm infection associated with the ingrown nail let your podiatrist know. Good luck!

About the same...: Patients relate similar relief of symptoms from both acute and chronic ingrown nails.

It could be possible: If a nail is deeply ingrown it may be painful to remove.