Found my answer! After some testing by adding a redirect URL to my .htaccess file, I found it was readable, but NOT writeable. I changed the permissions of the .htaccess file using sudo chown:
-rwxrwxrwx 1 _www staff 503 Apr 29 13:21 .htaccess
After I completed that step, I went back into the Dashboard, set my Permalinks to default, saved, and then set it back to the Post Name setting, saved, and went back to the site. Voila! It all worked!
What a pain! Took me 5 hours to figure this all out! BUT, I learned a ton about .htaccess, the code that you CAN do with it and the power it has. Pretty awesome stuff!
