Lining up the date and the top of the raised initial should just be a matter of giving the date a negative bottom margin - such as:
Code:
<style>
p {text-indent:1.2em; margin:0; padding:0; line-height:1}
p.date {text-indent:0; margin-bottom:-1.5em; letter-spacing:.1em;
font-style:italic; font-family:serif}
p.first {display:inline; padding-left:50%; text-indent:0}
p.first span {font-size:3em; font-family:serif}
</style>
</head>
<body>
<p class="date">APRIL 8</p>
<p class="first"><span>E</span>nter all ye who would... yadda yadda
yadda yadda yadda yadda yadda yadda yadda yadda yadda yadda yadda
yadda yadda yadda yadda yadda yadda yadda yadda yadda yadda yadda
yadda yadda yadda yadda yadda yadda yadda yadda yadda yadda yadda
yadda yadda yadda yadda yadda</p>
<p>And pay heed to those who are...</p>
...although I think Amazon barfs on negative margins??