After much searching I have hit a road block on the issues that I have been getting. I will try and explain everything the best I can.
My situation is that I have a PayPal register that needs to come back to my wordpress site to finish completion. However, PayPal will not automatically go back to my site unless its a htts/ssl page. Okay, fair enough. I download WordPress HTTPS in hopes to create a single or several pages that are SSL, and since I have direct control of my server, which is powered by Apache 2.2.22/osx server, I created a ssl self-signed certificate for testing proposes.
Now here is my dilemma, upon using force ssl on say a 'checkout complete' Page, I get a 404 error if I use a custom permalinks, by reading some of the previous 404 topics, it was recommended that I go back to default permalinks. So I did, and now I'm just getting a 'Index of /' in a https:// as the url reads "https://www.sampleserver.com/?page_id=522"
Any suggestions would be greatly appreciated.