I doubt they'll ever be free to reg. Always going to get picked up on the drop even if they're never sold. I think nominet are destroying this market with the decisions they've made. It's getting bad when far worse extensions are fetching more money.
I think the LLL's were in a bubble, it all depended on the quality of the domain. There's loads nowadays that are meaningless with X's and W's etc.. I registered a lot of them many years back, I was regularly selling them for up to £9k a time, it was all about waiting for the right company to come along.
I've sold 100+ decent LLL's over the years, I now only hold ~10 quality letter LLL's. They are a hard sell, they are not generic, so require a very specific buyer that typically needs to come to you, not the other way around.