I have what I fear may be a stupid #Linux question...
If I set up an ssh key, upload it to the server, and then disable password login...
When I want to ssh from another machine? How would I then upload that key to the server?

@hellomiakoda I usually use the enrolled machine to add the key in the new machines .pub file to .ssh/authorized_keys on the server. Its just a line of text in a file, so it can be edited with any text editor.

The advantage that has over copying the enrolled machine's private key to the new machine is that each key is now revokable if it gets lost/stolen/hacked etc.