There's always the chance that you don't get them, but that doesn't mean to just give up. This hobby has grown quite a bit, as you see mainstream geek sites showing off the latest and greatest in Hot Toys, but, to be honest, the custom market is still something of a well kept little secret. $1550 is a lot of money for three figures, but, while some may view it as a curse, you can also look at it as a blessing in disguise. It'll scare off some folks.
That being said, as far as the numbers thing goes, I'll restate what someone else said: The Cowboy's out. I've got him on my shelf, every other person who ordered him has him in his or her possession, and, for all intents and purposes, under normal circumstances, that'd be it. You missed out? Oh well; them's the breaks, kid; you snoozed, you lost, and the secondary market's the only way to go. That being said, Denny's breaking the mold and letting those who missed out get a second chance. Realistically speaking; how often can you say that happens, even with the larger companies? I'm not talking about improved releases, either, but, rather, actual, straight-up re-releases. I can only think of one or two occassions, maybe a few more, where Hot Toys has done that.
So, for you to begrudge them for not making even greater numbers is a little, well, disrespectful, in my opinion. The thing you have to remember is that Denny doesn't have the luxury of having a giant manufacturing chain like HT. He doesn't have factories; he's got a small team that shares the workload and puts a cooperative effort into completing each figure. 10 of these sets consists of 30 figures, and that's on top of the 100 or more Angel Eyes and Tuco figures that will be produced separately, along with however many head and outfit sets are produced.
Then, remember that they have a schedule to keep. If he waited for every eventual Cowboy purchaser to discover this hobby and for all of their orders to leak in, what would happen to those other fans? There are lots of people who are waiting for the Trek figures, the Fight Club releases, Kill Bill, The Wizard of Oz, The Last of Us, Breaking Bad, Memento, Die Hard; you get the picture. Point is, these guys work year round to get this stuff out there. One thing gets shipped, and the next release is getting finished. Why should those people have to wait because a select few want a massive run size on these figures?
I hope this has been somewhat enlightening, sir.
... Since they will be made, why not have a proper demand forecast. 
