The way paragraphs and lists are wrapped around big letters doesn’t look like beautiful typography to me: https://imgur.com/Yc7pkss unless it is trolling and I can’t comprehend tongue-in-cheek humour there. Well, anyway...
I can't speak to the OP's particular use of them, but initial capitals are a long standing typographical feature: https://en.wikipedia.org/wiki/Initial – CSS even has a ::first-letter pseudo element to help style them.
Yes, but then maybe some thought should be put by author into lists behavior around them on devices that aren’t phones? Just maybe...