public class InvestorMailing
{
    public string To { get; set; }

    public IEnumerable<string> Attachments { get; set; }

    public int AttachmentCount { get; set; }

    public long AttachmentSize { get; set; }
}

i have an IList<InvestorMailing> mailingList. if the attachment size is greater than x, then i need to split my object into chunks. is there an easy linq-y way to do this?

Edited:

this is how i'm generating my mailings:

        var groupedMailings = mailingList.GroupBy(g => g.GroupBy);

        var investorMailings = groupedMailings.Select(
            g => new DistinctInvestorMailing
            {
                Id = g.Select(x => x.Id).FirstOrDefault(),
                To = g.Key.Trim(),
                From = g.Select(x => x.From).FirstOrDefault(),
                FromName = g.Select(x => x.FromName).FirstOrDefault(),
                Bcc = g.Select(x => x.Bcc).FirstOrDefault(),
                DeliveryCode = g.Select(x => x.DeliveryCode).FirstOrDefault(),
                Subject = g.Select(x => x.Subject).FirstOrDefault(),
                Body = g.Select(x => x.Body).FirstOrDefault(),
                CommentsOnStatus = g.Select(x => x.CommentsOnStatus).FirstOrDefault(),
                Attachments = g.Select(x => x.AttachmentPath),
                AttachmentCount = g.Select(x => x.AttachmentPath).Count(),
                AttachmentSize = g.Sum(x => x.AttachmentSize),
                MailType = g.Select(x => x.MessageType).FirstOrDefault()
            }
        ).ToList();