I come at it from a different thought in which it is Ena on the bike photo text, and much later is actually Ena in the chocolate factory. If I had bought a brand new bike [bit of money there] I would take it first to see my intended, and give her a ride, with Ena taking the photo first.
Presumably Ena was his wife in the second one, and agreeing the handwriting is the same, suggests to me it was him just documenting the photo's at a much later date. During a 'Cuppa' chat of family photo's she was relaying to him what her job entailed in the factory.