Since TRAMP uses ssh by default, the real question you are asking is if you should use local or remote emacs to edit remote files. Right?
Is it considered better to use ...
There is no better, just that use cases differ for both local and remote editing.
What are some of the considerations involved in making this decision?
If you normally work with a variety of servers as part of your workflow, then use local Emacs with TRAMP. On the other hand, if you access remote server from a variety of clients, laptops, locations, or devices, then ssh into the server might be more convenient.
The size of the edits and any compilation needs also need to be taken into consideration. You can avoid large file downloads and uploads by using ssh. You probably cannot avoid this, say if you are editing in languages that are not natively supported by the server, but you have the tools locally.
If all your tools are local to your laptop, then using TRAMP makes sense. But if your servers mandate compilation on that machine (for security reasons), then ssh might be more appropriate.
Lastly, if your emacs usage is not dependent on mouse and other input devices (for multiple languages), then ssh is the way to go as it is optimized for keyboard interaction. Otherwise local Emacs with the full GUI interface is what you'd want.