Well, I've had mixed success with PhraseExpress. I've used that program for a long time to be able to assign hot keys to certain text (my different email accounts, frequent flyer numbers, etc.) and it works great. It does have options to also use hyperlinks and images, so I was hopeful I could assign icons/favicons and then have those associated with a hot key (eg Ctrl-T for a television favicon; Ctrl-Q for a question mark, etc.), so if you were entering a new calendar event, you could simply hit the hot key and follow it up with your desired text. When I have been successful, the relevant icons lose their color, etc.
Anyway, what I did end up doing for the moment, which actually works well, is the following, should anyone care or have add'l thoughts...
Randy's site for emojis is a good one, so I went through and selected various emojis comparable to my current flairs. I'm using Chrome, so on my bookmark bar I created a folder called "Cal icons" for quick access. In the folder I have direct links to my selected emojis. See the attached screenshot.
If I want to add a new calendar item, I click on my Cal icons folder, and select the icon I want to use, then when the link pops up, I simply hit "copy" (on the emojis site). Then I go to my calendar tab and simply paste the icon, followed by my desired text in the new calendar entry. It's actually pretty quick.
I suppose one could create a mouse script for each icon, then associate that script in PhraseExpress, and assign a hot key, eg by hitting Ctrl-T or whatever, the script would execute, go to the site for the associated icon, hit copy, and automatically bring you to your calendar with a new calendar entry open. The manual approach is sufficiently quick, I'm not motivated to fool with it. Still not giving up on PhraseExpress or a similar program, but at least I have an option I can live with...