Should edge cases I keep coming back to [v2]

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. Not sure if this is the right place to ask, mods please remove if it is not.

The trade-offs here are not obvious to me and I keep flip-flopping. For context, I am working with a pretty modest budget so high-end suggestions probably will not land. Looking for honest feedback, not validation.

Quick context: I am relatively new to this and trying to find my footing. Posting this here because the relevant subreddit has gotten too noisy lately.