Recommendations for edge cases after a year [v3]

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

The trade-offs here are not obvious to me and I keep flip-flopping. The trade-offs here are not obvious to me and I keep flip-flopping. Spent the last few weekends digging into this and the deeper I go the more questions I have.

Mostly thinking out loud — feel free to push back hard.