Fresh install redirects to www, breaking page loads

The way to pinpoint the specific cause of the problem you should configure your OS’s localhosts file to point the domain directly to the DO server. (don’t forget to use different browser or close and open the one you work with as they usually cache DNS results).

If in this configuration you are still getting redirections, the problem is with your web server/wordpress setup, but if thing work, you have some problem with DNS configuration somewhere.