Recommendations for this approach — am I overthinking this? [v2]

Quick context: I am relatively new to this and trying to find my footing. The trade-offs here are not obvious to me and I keep flip-flopping.

Long-time lurker, first-time poster.

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.