@mrkrndvs I like emoji particularly for posting to micro sites like Twitter and micro.blog where one is more constrained. I don't like it as much for some of the gymnastics I need to pull off, and most of which you mention. Not all sites seem to be able to handle them properly, and I often wonder at my decision to have used them in the first place. I've also noticed some issues with emojis in permalinks causing Brid.gy not to be able to send backfeed webmentions.

One thing that may make it easier to deploy them across your site is to bake them into the templates for your site (either into the post templates or into the post kind templates directly). This will allow you to use them quickly and easily and deploy them to thousands of posts at once with the ability to remove them later if you like. It'll also save you a huge amount of time hard coding them into your posts.