Should this approach — what would you do? [v2]

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. This came up at a meetup recently and the room was split, so curious what the broader community thinks.

Posting this here because the relevant subreddit has gotten too noisy lately. Spent the last few weekends digging into this and the deeper I go the more questions I have.

Long-time lurker, first-time poster. Not sure if this is the right place to ask, mods please remove if it is not.