Part of our motivation for not charging for files is that we weren't sure we could actually bring in money for the site this way.
We've had a donation link on the main page for a while now, which is cool.
But I'm thinking of actually working on some files that we would intend to sell. The series would work like this:
We'd have 1 hour-long or so free file to completely immerse someone in what the series is about, then that'd be free. But we'd have trigger, fantasy, etc. files that come after that, and charge for those to help pay for the site and such.
So I'm thinking of making a set of files just for my own subs.

Stuff for girls and guys who I trance regularly. But I might release it publically and the set of files would look like this:
File 1: Becoming Elena's (This file would walk you through deep trance, complete submission, and a bunch of other behavioral things I'd want my subs to do. This would be free as a sample of what's to come.)
File 2: Elena's Orders (A set of very enjoyable triggers for subjects delivered by me in a very personal style and with elements of loving control mixed in. We'd charge for this one, and the triggers would be used in the other files.)
File 3: A Day In The Life (This would walk the subject through a day as my sub, experiencing being used, pleasured, pleasuring me, all while having their brain deliciously ensnared and lasting effects imposed on their hypnotized mind. We'd charge for this.)
File 4: Udderly Owned (This file would be a lactation-heavy enslavement file where a sub is slowly made completely mine even outside of trance. Again we'd charge.)
File 5: Subliminally Hers (This would be free, like file 1, but would be for people enslaved by the other files and would be a subliminal for my subjects to listen to while they sleep or when working out. It would reinforce the submission and other cravings/elements)
So, see, the idea is that we give people a taste in one file, then charge for the better/more involving ones. Anyone think its a good idea? Anyone like the ideas above?