Help me decide between small purchases I keep coming back to [v1]

This came up at a meetup recently and the room was split, so curious what the broader community thinks. The trade-offs here are not obvious to me and I keep flip-flopping. Long-time lurker, first-time poster.

I want to write something more comprehensive about this later but starting with a quick post to gather thoughts.

Posting this here because the relevant subreddit has gotten too noisy lately.