I'm a big fan of telling folks how good Tips and Tricks HQ products are. I originally started my membership site (byobwebsite.com) with WP eStore and WP eMember. For a variety of nonsensical reasons I switched to WLM in May of last year (It seemed a bit more feature rich and I wanted an API so that I could customize my site without concern that changes in the plugin would require me to fix my customization).
It turns out to have been one of the top two worst decisions I've made in the development of my site. In my experience WLM NEVER works as advertised. You don't have to believe me either. Just take a look at the support forums and you will find hundreds of examples of this.
While they advertise it as being feature rich, many people find that those features simply don't work. The drip content feature? Doesn't work. A couple months ago on the paid Wishlist Insider membership arm of WLM their own authorized developers were warning people not to upgrade to the latest release because it was breaking their sites.
They also advertise their API. Except that they regularly change that API and anything you've done in the old one FAILS in the new one. What's worse, they don't tell you that they've changed it in the release notes so you upgrade to the latest version and BAM your site no longer works.
Not a single upgrade has worked for me as promised, and EVERY upgrade has introduced a new set of bugs that you have to trouble shoot. Seriously, upgrading that plugin feels like the most dangerous thing I do on my website.
Those guys spend way too much time and resources on marketing and far too little time and resources on testing and debugging their software and on customer support. They recently published an article on their "Insider" site on how to run a successful membership site. It perfectly articulates their model of spending 80% of their effort on marketing and sales and 20% of their effort on meeting their customers needs.
Run, don't walk, away from that plugin. If you value your membership base you won't use that software.
If I could find a smooth upgrade path from WLM to WP eMember I'd do it in a heartbeat.