I think you will find Tags to address most of what you are looking for, for business reimbursement and business expense identification. You don't say what version you using, but assuming HBRP, then you will find a robust set of business categories. Then you would only need tags for full-time business reimbursements.If you suspect your file is corrupt, run a File>File Operations>Validate to ID and resolve issues. As a side note, I would recommend suspending the use of mobile cloud sync.
Robert Freeman said: Quicken has preselected tax items associated with categories. Business categories are mapped to schedule C primarily whereas non-business categories are mapped to typical 1040 items.