I've been trying to configure my mail to work for several days. I installed the configure smtp plugin and setup everything to work. I was having issues with gmail receiving email from my server period until I setup SPF. After setting up SPF gmail had no problems with mail from my server.
In configure smtp I configured WordPress to use smtpauth with an email account I setup specifically for wordpress to use. Everything worked correctly and the email is sent to my gmail account with no issues when I test from the plugin. WordPress still does not send any emails even though it works when testing the plugin. The site I'm building is using BuddyPress and there will be a lot of users registering so the can use the site as soon as I launch. None of them will be able to confirm their email after registering on the site.