Symptoms
Run into role assignment validation error, when attempted to validate whether the datafield was empty, and if so, needed to be assigned to another (admin) role as a backup, in order to prevent Folio to "disappear".
Diagnoses
Email would not execute if field equaled null.
Resolution
Injected the following in to Visual Studio that corrected initial email error to send if field is null.
if (this.EmailMessage.From.ToString() != '')
{
//SEND ONLY if To IS NOT NULL/EMPTY
SmtpMail.Send(this.EmailMessage, K2.ProcessInstance.Logger)
}