My 2011 SFH purchase had payments a bit above rent, partly because I only put down 5% and had to pay a higher rate and PMI, and partly because it was a teardown on a huge lot without great rental value.
About a year later I did a cash-in refi and my payment dropped from 2450 to 1950, and that knocked it well below rent value, and a huge positive after accounting for tax benefit and the principal part of the monthly payment.
My 2015 house and 2016 condo purchases were 20% down and slightly cash flow positive from the get-go.
Cash flow is an arbitrary measure though. Given the many benefits of homeownership, when payments are below rent that’s a sign RE is a screaming good buy, but many excellent entry points will be cash flow negative.