public class Mailing
{
    public string To { get; set; }
    public string AttachmentPath { get; set; }
    public int AttachmentCount { get; set; }
}
giving this structure i have a IList<Mailing> mailingList where To has dups and the AttachmentPath is unique per To.
i need to send emails to the mailingList where each unique To has multiple attachments (ie AttachmentPaths).  
this partially works -- i can get the attachment count and iterate and add attachements as i need but i think this is ugly. i also need to limit a single email per group of attachments where the below completely breaks.
var investorMailings = (from m in mailingList
                       group m by new
                               {
                                   m.GroupBy,
                                   m.To
                               }
                           into g
                           select new DistintInvestorMailing
                               {
                                   To = g.Key.To,
                                   AttachmentCount = g.Count()
                               }).ToList();
any ideas?