As others have already mentioned, if you are arrested and be forced to give the keys then it does not really matter what kind of keys or how many of them you use; you'll have to give them away anyway. So you may want to think of other approaches in order to protect you/your work (e.g. steganography or having your server in another country, away from your country's jurisdiction, to which you connect from your laptop, in which laptop you store nothing).
Now, to the point of your question, the short answer is yes, they should all be different.
The reason is that a single password can grant access to all of your protected data (server, laptop, 1Password) if it gets compromised. For example, a knowledgeable adversary could just target your server from the internet, exploit the software on it, gain admin level access, extract the key (e.g. from memory or by installing a bootkit), then visit your home while you're out, copy your laptop's hard disk without leaving any trace and then use the password to decrypt your laptop's copied disk. And you wouldn't even know. Which also means that they could do it again and again, getting access to any new info you put in your computer. (I guess I don't have to explain the impact this will have, if the same password is the master password for 1Password).
On the difficulty of remembering a long password, that's easy: use a passphrase. An easy way to find one is to pick a song that you remember well, get one sentence from the song, change some letters to their optical similar numbers (e.g. o to 0, A to 4 etc), capitalize a couple of the letters and you have a pretty strong passphrase. For the next system you may use the next sentence of the song or a sentence from another song.
Whatever you do, though, I would suggest that you coin a method about how you derive such passphrases, so that your passphrases are consistent and make sense to you and you don't get locked out of your data eventually.