Daily thread: small purchases — am I overthinking this? [v5]

This came up at a meetup recently and the room was split, so curious what the broader community thinks. Spent the last few weekends digging into this and the deeper I go the more questions I have. Long-time lurker, first-time poster.

Quick context: I am relatively new to this and trying to find my footing. Been thinking about this for a while and curious what the community thinks. This came up at a meetup recently and the room was split, so curious what the broader community thinks.