So after all this, I'm still left uncertain what I should do (deduct the stuff on my 2018 and 2019 returns which I'm in the process of filing), or reimburse myself in 2020 and deduct it on the 2020 return.
Regarding your comment on raising red flags, why would it raise a red flag? The IRS doesn't see any of my accounting details unless I'm audited. Are you just saying that if I were audited, the IRS would have an issue with reimbursing myself this late? What would be the issue they'd have and the associated consequence?
