No, they are not difficult to appraise, especially when they are pronounceable. This domain has an estibot value of $1200 and can be sold for a reasonable figure if market properly. Here is an example, in the fitness niche, is a good place to start.
Domains for me is like collecting fine art, especially when the artist has died the pieces becomes very unique. Such is the case with LLLL domains, there are no more variants that can be generated. So 10 years from now the ones you paid $700-1200 for will be $7000-12000. That's just the name of...
Hey, that calls for a lot of discipline and vision. Although, if he had started purchasing domains in 1985 his portfolio would not have "crappy" names. So, we can safely rule that one out
Well, for a guy to own 300,000 domains, that's no normal person with a little bit of cash hoping to hit it big. He is a big guy. Let us say he paid a $1 for one domain that's $300K! And we cannot say he has sold some...because he still has all of them. That's unique.