Oh, I know this. I've gather about all the same information from the various webcomics I read, and their occasional posts about how much it actually costs to run so many. Which is why a lot of those same webcomics do preorders, to find out how many people are actually interested in getting it. Or, they simply ask. Generally, people will say whether or not they are interested or not. True, not everyone who says they'll buy something will buy it, but on the flipside, some will.
And if it's 2-5k up front, well, set the prices accordingly. I once paid $39 for the signed hardcover of a $15 paperback because I really liked the webcomic. And it was 72 pages long. Albeit, full color, but still point stands. I've played BM for a lot longer than it took me to read that webcomic.
Not to mention, with physical books, you can charge extra for random things, like getting so-and-so's signature in the book, or you can number so many of them, or say "I'm only signing the first 50", or whatever creative thing you come up with.
The difference is, since it is a web comic you already KNOW you will like it, you already know how you value the content. With Toms offering you are taking a bit of a gamble on just what the value of the content will end up being. So we are left with Tom needing to spend time establishing his story telling credentials just so he can take a shot a publishing a series of short stories? Guys that do web comics tend to dedicate hours upon hours a week to get things up and running, for months or years before publishing a collection is a practical reality.
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