1: cmd-ctrl-space, visit the gear menu and behold the huge number of Unicode ranges you can turn on and off in the 'Customize List' pane
I started by picking a 'shortcut tag'--a single character that prefixes all my shortcuts that aren't typo replacements. This prevents issues like having a shortcut trigger in the middle of writing a command or a piece of code. These days I use ';' and then follow the trigger with a space (e.g. ';dt ' is the full shortcut), as that doesn't come up in normal writing. (Annoyingly, the default substitutions in Mac OS/iOS don't respect these--if you create a trigger named ';dt ', it's going to try and trigger every time you write 'dt', with or without the semicolon and space. Probably because it's tied to the Autocorrect engine, which is very aggressive.)
Couple I've found particularly handy:
;dt -> Prints the date as 2021-Mar-19 (very useful for quick-naming backup files!)
;DT -> Prints the date as 19 March, 2021 for more formal writing
;chr -> Prints "Cheers, <name>" as a quick way to sign an email
;fullstack -> Prints the subCA and root CA certificates in PEM format for the CA we usually use
;rarr -> Prints the "→" character, which is handy for nice lists. :)
I also take advantage of Typinator's variable system. So I can enter ';ldif ' and it will prompt me for a user's name and UID values, then construct an LDIF file for use in adding them to LDAP. I have a couple boilerplate email responses in there as well that will just blow out the standard response with spots to fill in the user's name, for those "did you turn it off and on again" emails you write 50-odd times a day.
Johnathan -> Jonathan // or whatever common misspelling you have for your manager or coworker. I don't need it now, but can be a good stop-gap
teh -> the // For some reason auto correct doesn't catch this very common mistake
adn -> and // same
thx -> Thank you! // brevity + professionalism
thxa -> Thanks in advance! // it's surprising how effective this phrase is at getting someone to do anything
On my iPhone:
ducking -> fucking
Lol -> lol // that capital L bothers me
omw -> On my way!
omwh -> on my way home
I used macOS shortcuts for industry-specific terms that were common for me (typing out “Oracle Hyperion EPM HFM Service” several times a day gets boring fast). Nowadays I do something similar on Windows with AutoHotKeys combinations.