What do I do if I do not have proof of an expense?
The law allows you to use indirect or third party proof except in the case of entertainment and travel to validate your expense. So for example if charitable, secure a letter from the church instead of copies of your checks to the church to validate charitable, or in the event of medical secure copies of letters from doctors and medical hospitals.
The “Cohan” rule from the court case allows taxpayers to utilize this principle.