How community norms — am I overthinking this? [v5]

Looking for honest feedback, not validation. The trade-offs here are not obvious to me and I keep flip-flopping. 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. Been thinking about this for a while and curious what the community thinks. Posting this here because the relevant subreddit has gotten too noisy lately.