Help me decide between workflow tweaks on a tight budget [v4]

Mostly thinking out loud — feel free to push back hard. There is a lot of conflicting advice online and most of it is from 2019. There is a lot of conflicting advice online and most of it is from 2019.

This came up at a meetup recently and the room was split, so curious what the broader community thinks. Posting this here because the relevant subreddit has gotten too noisy lately. Spent the last few weekends digging into this and the deeper I go the more questions I have.