Best long-term planning — am I overthinking this? [v1]

The trade-offs here are not obvious to me and I keep flip-flopping. Been thinking about this for a while and curious what the community thinks.

Maybe an unpopular opinion but here we go. Posting this here because the relevant subreddit has gotten too noisy lately.

Long-time lurker, first-time poster. Maybe an unpopular opinion but here we go.