In June, my Cosair Scimitar went to mouse heaven, so I bought a new Redragon Perdition M901 gaming mouse for playing Final Fantasy XIV. When I first tried to set up all of my key combinations to the side mouse buttons, I found that my key combo buttons wouldn't work, or would only work every few clicks.
After doing a little bit of digging, including using this very cool website to show me my keyboard events, I discovered that the key combo setup in the Redragon software was working, but it was sending the key events too quickly to register correctly in FFXIV.
I ended up getting my mouse buttons set up by recording the combos as macros with a 10ms delay. Record your macro of you typing, for example holding down alt and then tapping the 1 key. Turn on the option "Insert Default Delay" — the default 10ms delay amount should work just fine. You don't need (or want) "Record Delays Between Actions" on.
Update September 21, 2021: My Perdition M901 mouse mysteriously stopped reporting itself as a valid USB device in August 2021, so I had to buy myself a new gaming mouse. Now I'm using a Logitech G600. For the life of me, I couldn't find anywhere in the Logitech GHub software that I could set up a simple mouse macro like mapping one of the side buttons to
Alt + 1. I'm not even sure that software can setup key combos involving some of the key modifiers (like alt or ctrl). So I had to go back to the older Logitech Gaming Software, and that still allows for simple key combinations like that, and seems to be working fine for the past couple of months.
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