Hey there, @mmdonovan
Bo here from Shopify Support!
I am sorry to hear that you have been experiencing issues contacting support. When on the Help Centre page, you should see Support > Contact Support in the main menu or there's a Contact Shopify Support button near the end of the page. The Help Centre will try and suggest guides first to resolve your query, however, if none of these suit your needs then please keep clicking the Contact Shopify Support button at the end of the page instead.
In some cases, Chrome extensions and cache can interfere with the Help Centre's login/authentication process and you might experience a "loop" when trying to contact our support. If this happens, I'd recommend clearing your cache or to log out of your Help Centre account and access our support as a guest instead as shown in this short video. Our advisors can authenticate the account later if needed or our Facebook and Twitter support would be happy to help instead. You are welcome to contact us here on Twitter or here on Facebook.
Of course, if there is anything you would like me to help you with here, let me know!
All the Best,