Should late-night thoughts on a tight budget [v2]

Long-time lurker, first-time poster.

Posting this here because the relevant subreddit has gotten too noisy lately. There is a lot of conflicting advice online and most of it is from 2019.

Mostly thinking out loud — feel free to push back hard. Spent the last few weekends digging into this and the deeper I go the more questions I have. For context, I am working with a pretty modest budget so high-end suggestions probably will not land.