[Excavator]

Hello Chell,

So I'm guessing there isn't any way of doing it 'automatically' using only CSS?

I think first-letter can still do a lot for you. Span might be easier to do but with a little setup ahead of time, it would be easy to apply first-letter to new entries.

Something like this -

p:first-letter {
	margin: 5px 10px 0;
	padding: 18px;
	float: left;
	font-size: 4em;
	border-radius: 5px;
	box-shadow: 0 0 10px -2px #999999;
	background: #3399FF;
	color: #fff;
}

Your quote marks might work well as an actual background image.