I put all expenses on my corp card and that links to the expense system. We are required to use the corp card for all hotel, air and rental car expenses. The expense reimbursment goes straight back to the card and not to me.
Therefore, I cannot expense a hotel item unless the expense hits the card.
An old expense is reimbursable but you may need to get approvals from seveal levels up. That is a pain so I would ask for the 10K in points.