Worst long-term planning that nobody talks about [v3]

Quick context: I am relatively new to this and trying to find my footing.

Long-time lurker, first-time poster. For context, I am working with a pretty modest budget so high-end suggestions probably will not land. Mostly thinking out loud — feel free to push back hard.

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.