Nearly every time someone suggests against this it's not about issues in setting up the server or receiving emails. It's that many popular providers don't trust random IP addresses sending emails, especially those that 'look like' common spam (such as order invoices from common e-commerce sites like Woocommerce or Shopify).

From an inbox perspective these often look like cold outreach (you've never emailed this company before and the first email they send to you is after you order something) so it's suspicious, and being from a trusted platform helps pass the test.