Combining CSS And JS In Master Pages And View Pages With SquishIt?

How do you implement SquishIt to bundle Css/Js across View Pages and Render it in the Master page? I thought I could use a ContentPlaceHolder above the Render portion, but there seems to be some odd behavior where it sometimes adds 3 files (1 in the view page and 2 in the master page) but other times will ignore the file added from the View Page.

Index.aspx
<asp:Content ContentPlaceHolderID="CssFiles" runat="server">
<% CssHelper.Add("home.css"); %>
</asp:Content>
Site.master
<asp:ContentPlaceHolder ID="CssFiles" runat="server" />
<% CssHelper.Add("reset.css"); %>
<% CssHelper.Add("master.css"); %>
<%=CssHelper.Render() %>

My current solution is a Static wrapper around SquishIt's static Bundle class that keeps the BundleBuilder in HttpContext.Current.Items.

I'm curious if this has been done successfully and how so.