Wait only if the phone still feels good
Waiting makes most sense when there is still enough usefulness left to outweigh the likely drop in value.
Trade-in guide
This is usually a timing question about two curves moving in opposite directions: how fast your phone's value is likely to fall, and how long it will still feel good enough to keep.
Quick answer
If you are already pretty sure you will upgrade soon and the phone is beginning to slip, waiting often means accepting less value and a worse user experience. If the phone still feels fine and you are not sure you even want to replace it, waiting can be reasonable.
Waiting makes most sense when there is still enough usefulness left to outweigh the likely drop in value.
If you already know a replacement is coming soon, acting earlier is often cleaner.
Phones with falling battery life rarely feel better after another few months of use.
If you are not sure you even want to switch, waiting can be the wiser move.
Examples
If the replacement plan is fuzzy and the current phone is still fine, waiting is defensible.
This is one of the strongest cases for trading sooner rather than later.
Waiting may be reasonable if the current phone still feels good and you want more clarity.
FAQ
Waiting is more reasonable when the phone still feels good enough and you are not yet sure a replacement is needed.
Usually when the phone is already getting worse and you are likely to replace it soon anyway.
Not exactly. The real question is whether current value and current frustration are aligned strongly enough to justify acting now.