Anyone else long-term planning — what would you do? [v1]

Long-time lurker, first-time poster.

Mostly thinking out loud — feel free to push back hard. I tried three different approaches and none of them felt quite right.

For context, I am working with a pretty modest budget so high-end suggestions probably will not land. This came up at a meetup recently and the room was split, so curious what the broader community thinks.