Paid for a subscription (iCloud)

As a self-employed person in secondary occupation (sole proprietor), it does not matter which account you use to pay (because you are a single entity for tax purposes). In both cases, you book the Apple iCloud invoice as an expense and enter the percentage of business use (for me, that's 85% because I mainly use it to store all my documents (photos of site visits, customer evidence, Excel spreadsheets with calculations, SketchUp 3D drawings, etc.) so that I can access the data everywhere.