Looking for long-term planning on a tight budget [v2]

I tried three different approaches and none of them felt quite right. Mostly thinking out loud — feel free to push back hard. This came up at a meetup recently and the room was split, so curious what the broader community thinks.

Maybe an unpopular opinion but here we go. Maybe an unpopular opinion but here we go.

Spent the last few weekends digging into this and the deeper I go the more questions I have. Quick context: I am relatively new to this and trying to find my footing.