Definitely. I'm waiting exactly for that moment.
I spent the hundred bucks...no regrets. It's less than ten a month. I spend many hours on here...it's pennies an hour and cheaper than almost anything else I could do. And the included instructional videos are like a library of training, way more than I ever even use, personally I think it's completely worth it.
Radiohead put out an album in which they asked people to pay whatever they thought the album was worth. Some were willing to pay a lot more than the standard price of an album. Maybe if Chess.com adopts a similar policy and presents it the right way they could achieve an increase in profits which would allow them to make improvements as they see fit. If I could I'd spend a million or so on the membership.
Sometimes one person can make all the difference in the world, so to speak.