Should gear recommendations [v5]

Not sure if this is the right place to ask, mods please remove if it is not. This came up at a meetup recently and the room was split, so curious what the broader community thinks. This came up at a meetup recently and the room was split, so curious what the broader community thinks.

Been thinking about this for a while and curious what the community thinks. Quick context: I am relatively new to this and trying to find my footing.

Looking for honest feedback, not validation. The trade-offs here are not obvious to me and I keep flip-flopping. Not sure if this is the right place to ask, mods please remove if it is not.