The main issue I have is password that I don't use often at all. I usually can't remember them, or if I can, I cannot associate between password and website.
Yet another reason I love using a password manager[1]. Besides letting you have unique passwords for everything (which is a must), it solves the "What the heck was the password for XZY?" issue when you haven't logged into XYZ in 6 months.
People really should just use a password manager. Yes it's a pain some times (mainly using mobile) but that's just something you live with. The rest of the time though it's way better than trying to remember silly thing like "Capitalize the second letter of each word" or "Replace the last letter with a digit that denotes the number of words in the phrase"[2].
Long passwords are a solved problem and the solution is not reinventing the Caesar cipher, it's to have a single long diceware password and use a password manager for the rest.
Oh and enable two-factor auth everywhere that allows it and vote with your wallet to choose businesses that do. For example, if your bank doesn't support it, find a new bank.
[1]: I suggest KeePassX: https://www.keepassx.org/
[2]: The article suggests things like this to make sure your password unique/dictionary proof. Forget that and just use the password manager directly.
* Dropbox (which lets me recover a deleted file up to 30 days) * Time Machine * BackBlaze * Monthly HDD clone
Pass looks interesting though the convenient way of using it (plaintext name for each site) leaks information. If you're willing to give that up then it sounds like a good idea.
if you're worried about the security of that you can even take it 1 step further and add a keyfile to your login requirements. you could just store the keyfile outside of dropbox on the devices.
I use the former, since I'm on Windows, and use VMs for any dev related work. KeePass seems to have a good system in place for synching versions. Using GDrive, if I edit my pass on one machine when I try to add a new password from a second machine I get prompted to either Sync the file first or just completely overwrite it. I've yet to encounter an issue where KeePass gets confused as to what's changed and end up losing passwords in the process.