Looking for long-term planning — what would you do? [v5]

I tried three different approaches and none of them felt quite right. Not sure if this is the right place to ask, mods please remove if it is not.

Been thinking about this for a while and curious what the community thinks. I tried three different approaches and none of them felt quite right.

I tried three different approaches and none of them felt quite right. I want to write something more comprehensive about this later but starting with a quick post to gather thoughts. The trade-offs here are not obvious to me and I keep flip-flopping.