Anyone else small purchases — what would you do? [v3]

Not sure if this is the right place to ask, mods please remove if it is not. Maybe an unpopular opinion but here we go. This came up at a meetup recently and the room was split, so curious what the broader community thinks.

Mostly thinking out loud — feel free to push back hard. The trade-offs here are not obvious to me and I keep flip-flopping. Not sure if this is the right place to ask, mods please remove if it is not.

Been thinking about this for a while and curious what the community thinks. For context, I am working with a pretty modest budget so high-end suggestions probably will not land.