I've wasted waaay too much thought on that thing: why won't the founders just release an API like they originally promised, why did they delete the entire Freewrite forum full of many complaints right before a new model was released, why... and here I am... sucked in again, whining... publicly. Jeez.
Anyone out there thinking of buying one these things, my gentle suggestion is don't. Really just don't. I'll let you borrow all my wasted time so that you don't have to waste yours.
The most gracious thing I can say is that wasting my precious time and hard-earned cash on a Freewrite taught me a very important lesson... do not be seduced by slick marketing and a new device to solve what is at its heart a self-discipline problem.
On a positive note, it got me into exploring the dead art of writing on actual typewriters. A typewriter is a good deal more useful than a Freewrite, version control on the page for example. I can edit and rewrite with a pen. Good times.
I'm a professional screenwriter and often use a typewriter for first drafts or when I'm super stuck on something or procrastinating on a hard deadline. It's a good way to get things moving. I OCR the pages into emacs and fountain-mode to rewrite until the inevitable time comes when production needs the script in Final Draft... which is a sad moment, but so it goes.
I took an unfortunate road filled with regret that led to way of working that I love. So there's that.