Join the club. I started my first membership site about 9 months ago and it was anything but easy. However, now it has moved into the realm of profitable and we have worked out may of the kinks.
Membership Website Rule #1 - Keep it simple
I used the following software: Druple, Moodle, Ning, DotNetNuke and experimented with others. Finally, I decided to invest in a wonderful membership plugin for Wordpress and I moved my membership website to Wordpress and I have been sooooo happy.
After more than 9 months I finally decided to start sharing my membership website experience and expertise, although I am still learning.
Here is the free blog (no membership) called membership website that I started to document the membership website best practices that I have been developing.
Visit membership website scripts for information about software and scripts.
The membership websites blog is going to be where I publish all this information - if you are interested in how to develop income with wordpress membership sites, be sure to bookmark that website and stop back often.
In case you are wondering: I might make the whole thing into a subscription-based membership site eventually, but for now it is free and if I make a little something off of the affiliate ads, I am happy.