And, for my money, Chief Herman's Next Big Thing is the better collection.
In both cases, Cheapass took games that originally were in advertisements and convention and on their website and then made a collection of them.
However, James Ernest had more practice making games by the time the second collection came out. And it shows. There is definitely more variety in Chief Herman's Next Big Thing.
And, for me, these collections are as much, if not more, about reading for enjoyment. I'm interested in game design, both mechanics and theory. More variety is more interesting for me.
However, what really makes Chief Herman's Next Big Thing shine for me is that it includes Darwinian Poker, also published as Lamarckian Poker. It's a really good game that I have played a lot with a wide variety of people. I bought the collection to read but including a game that I will suggest and look forward to playing is a big bonus.
I think it's safe to say that there won't be a third Chief Herman collection. For one thing, it doesn't fit into their current business model. For another thing, the Internet has changed a lot since 2003.
Cheapass's website has a free game section that serves as the successor for the Chief Herman collections. And, quite frankly, has a higher quality of games on a whole. The Poker Suite, a collection of fourteen card games, is quite literally a miniature Chief Herman collection.
The Chief Herman collections are not a bunch of brilliant games destined to become classics. However, they are testament to the ingenuity and determination of a quirky little company.