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Account management
RE: We do need it to print, but not something that goes in the "Customer Message" area, because it's a dropdown list of messages you can make and choose from, not a text box.
Right. OK, needs to print and not from a pick list.
RE: We would need potentially each message to be different, reference each specific job the estimates are for.
Why not use the Description column on the Invoice/Estimate table? Seems the perfect solution based on the needs you've stated...