HubSpot Automation and API Questions for Sales Development Experts

Questions for Hubspot Experts: Context - I run an outsourced sales development shop and am working on some automations to run everything out of my own CRM so that I dont have to run multiple systems. Q1: Why isn't my automation working? Q2: Am I thinking of this the right way to track meetings booked with new deals? I think yes because it'll track revenue generated better. Q3: Are there any good API's that easily give me access to a clients calendar so I can book through Hubspot directly without having to use their calendly? Loom recording: https://www.loom.com/share/e8383d99ec8d4d95ae4bdc723a6eeb6b?sid=54bb329b-68dc-4afa-853a-f97d690d4402 Thanks in advance