Does Ramp/Stack connect to platforms like Square for income/transaction reports, and what's the current roadmap for integrations beyond QuickBooks?

Not yet, but it's planned. Today the first iteration connects to QBO. Soon, integrations will expand beyond QuickBooks to Xero, Intacct, and NetSuite, with the integration list growing over time (within roughly the next month or two for the accounting platforms). Beyond that, the team plans to integrate with payroll providers, e-commerce systems, and other sources that feed the GL, so Ramp can pull data automatically, draft journal entries, and leave the user just to post to QBO.