Reminder that gear recommendations — am I overthinking this? [v5]

Spent the last few weekends digging into this and the deeper I go the more questions I have. I tried three different approaches and none of them felt quite right.

The trade-offs here are not obvious to me and I keep flip-flopping. There is a lot of conflicting advice online and most of it is from 2019. Been thinking about this for a while and curious what the community thinks.

Spent the last few weekends digging into this and the deeper I go the more questions I have.