Most things boot owners try only provide temporary relief. They may cushion the discomfort for an hour or soften the leather on the surface, but they don't address the actual shape mismatch between your foot and the boot.
Thick socks add padding around the problem but don't move the leather. The pinch is still there underneath the cushion.
Conditioning spray softens leather but doesn't change its shape. The stiffness comes back once the leather dries.
Breaking them in applies pressure everywhere at once instead of targeting the one spot that needs to move. You're treating a localized problem with a general solution.
The cobbler stretches the whole boot once and hands it back. At $50-65 per visit, the cost adds up — and on thick cowboy leather, the stretch often creeps back within a few weeks.
That's why the same spot keeps hurting. The cause hasn't been addressed. Just the symptoms.