The membership options got changed to what they were now several months ago, to make the system less confusing. Also, I would assume the staff realised they wouldn't be able to support a set of members based on a one-time payment.
What happened to the lifetime Diamond option?

I'm imagining that it was a combination of it not being all that popular and the fact that it's hard to get any repeat business from it.

Well, true, no repeat business, but if you have a guy like me who doesn't really wanna pay $100/year, but pays the $30, then that adds up to almost 17 years or so of business right there on the spot. Of course, if they don't offer it again one day, I will continue to do this, and in 16 or 17 years, they will have $500...I think they ought to offer it still, but anyway. Plus, that is one of the cool features, I believe...people who have paid their way in...they are a fluent part of the system...never have to worry about it ever again...

What if one month you'd rather have the cute crown next to your name instead of the diamond? The diamond is classy & of course will "pull massive tail" but maybe just maybe sometime you'll want to feel like a King!

What if one month you'd rather have the cute crown next to your name instead of the diamond? The diamond is classy & of course will "pull massive tail" but maybe just maybe sometime you'll want to feel like a King!
The Diamond pulls massive tail? I don't want massive tail. Which one pulls skinny hot tail?
I think it's pure economics, $500 isn't enough money to cover $95 per year for the average lifetime.

Sure it's economics, but a guy like me doesn't really want to pay $95 per year either...the other way around was like paying around 20 years of standard in one bulk...that's pretty good. I am sure they are getting the $95/year from some people...I just don't think that it is worth $95 a year, especially from a guy like me who works a regular job and has bills to pay. Maybe if I made more money...I know the arguments, it is around .25 a day for the diamond option...but at the same token, there are other things in life I would like to invest in. Truly, I don't feel led after this post to continue in on this forum...I was hoping, maybe sometime in the future, with a tax check, I could pay for it in one sum. Oh well... :-)

The lifetime diamond membership greatly increased in value when the membership scheme was changed - i.e. at the very moment it became unavailable as a membership option for new buyers.
It used to be that you could buy a lifetime membership, but Chess Mentor was still an extra time-limited subscription - an 'add-on.'
With the re-org, Chess Mentor became a built-in part of the Diamond membership, so all of a sudden, a lifetime diamond membership also became a lifetime subscription to Chess Mentor.
There was an interval of a month or two between the announcement of the impending changes (and the revelation about the possibility of life-long Mentor) and the actual change - which would of course bring an end to the addition of new lifers, so I think a number of people dug deep and bought a ticket before the train left the station for good.
There used to be an option for a lifetime Diamond membership... I had debated that one day when I had the money, I was going to purchase it, but now it looks like it is only a yearly thing. Is there no more $500/lifetime Diamond options? Even then, it was like paying for 20 years of membership at one time, but I thought it was a cool investment. I think even now, they should still have that option. Of course, now I cannot pay for it. But there will come a day when I can afford it, and I really like this site. Just something to consider. If it won't happen, I guess I can continue paying for the gold membership! :-)