Thanks for confirming!
I found that my above version was causing intermittent use of the shortcut to be missed in Chrome (probably due to the pause). So I updated the macro(s) to this form which only triggers in Outlook online and no other Chrome tabs, and that seems optimal:
I wasn't going to mention it but my actual situation is even weirder than just remapping Option to Command intermittently. But, since you asked... 
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What I've actually done is remapped Fn (The Globe Key) to Option at the OS level and then mapped Option to act as Command using Keyboard Maestro for most Command shortcuts I use regularly.
How did I arrive at such a strange configuration? Well, my first computers were Windows computers which have keyboards set up like this:
VS Mac keyboards that are set up like this:
On Windows, Ctrl (which more-or-less has the functionality of Command) is located by the pinky which is a much more logical/comfortable placement IMO. For example, the shortcut ⌘⇧V to paste text without formatting on Mac is just gross to type. I also greatly prefer CtrlTab and Ctrl⇧Tab for cycling through tabs in the browser on Windows. With my remaps I can do that with the "same" keys on my Mac. On Windows, I also loved the AltTab, Alt⇧Tab shortcuts for cycling through programs, so it's great that you get similar functionality with ⌘Tab on Mac (especially with the handy AltTab tool).
More generally though, between Tmux, Neovim, and the 57 other programs and extensions I use regularly, it's gotten to the point that I pretty much have to consult Defkey to see which programs already use a given shortcut before I define a new one (so that I don't accidentally configure one I'll regret). These days, to avoid clashes, I often use two or three modifier keys for my shortcuts, and typing ⌥⇧<key> or ⌥⇧⌘<key> is a lot more comfortable when Fn is replaced by ⌥.
Anyway, that explains why this is one of my all-time favorite cartoons:
