When Mickey's colleague was tasked with changing <br>s into newlines, he wanted to cover all the bases. Since <br />, <Br />, <bR />, etc. are all valid HTML, he clearly had his work cut out for him.

Damn case-sensitive string comparison, he must've thought. This could be so much easier! Oh well, I guess there's only one way to do it... brute force, baby!

'Replace <br /> with vbCrLf
If LCase(strTagLess).Contains("<br>") Or _
  LCase(strTagLess).Contains("<br/>") Or _
  LCase(strTagLess).Contains("<br />") Then
    strTagLess = Replace(strTagLess, "<br>", vbCrLf)
    strTagLess = Replace(strTagLess, "<Br>", vbCrLf)
    strTagLess = Replace(strTagLess, "<bR>", vbCrLf)
    strTagLess = Replace(strTagLess, "<BR>", vbCrLf)
    strTagLess = Replace(strTagLess, "<br/>", vbCrLf)
    strTagLess = Replace(strTagLess, "<Br/>", vbCrLf)
    strTagLess = Replace(strTagLess, "<bR/>", vbCrLf)
    strTagLess = Replace(strTagLess, "<BR/>", vbCrLf)
    strTagLess = Replace(strTagLess, "<br />", vbCrLf)
    strTagLess = Replace(strTagLess, "<Br />", vbCrLf)
    strTagLess = Replace(strTagLess, "<bR />", vbCrLf)
    strTagLess = Replace(strTagLess, "<BR />", vbCrLf)
End If

Mickey wound up replacing his colleague's code with:

Regex.Replace(html, "<br ?/?>", vbCrLf, RegexOptions.IgnoreCase)