Why long-term planning after a year [v4]

For context, I am working with a pretty modest budget so high-end suggestions probably will not land. Maybe an unpopular opinion but here we go. There is a lot of conflicting advice online and most of it is from 2019.

I tried three different approaches and none of them felt quite right. Looking for honest feedback, not validation. Spent the last few weekends digging into this and the deeper I go the more questions I have.

Posting this here because the relevant subreddit has gotten too noisy lately.