Should gear recommendations on a tight budget [v5]

I want to write something more comprehensive about this later but starting with a quick post to gather thoughts. This came up at a meetup recently and the room was split, so curious what the broader community thinks. Not sure if this is the right place to ask, mods please remove if it is not.

Spent the last few weekends digging into this and the deeper I go the more questions I have.

I tried three different approaches and none of them felt quite right.