Gary, I'm not a businessman, and so my assumptions about them are just that -- assumptions. But, in the case of Maytag, I was (and am) assuming that he likely set up his whiskey-distilling operation independent (at least financially) of his brewery for the simple reason that its potential failure could not then impact the existing successful business. If so, then his other successful enterprise(s) would have no bearing on whether or not income from Old Potrero was desireable early on.
I've read some of Maytag's statements about his views of historical rye whiskey, and have found them mostly unconvincing, as he seldom provides any evidence beyond his stated convictions -- including that, for example, his 'authentic' whiskey should be from 100% rye grain. Gary, you're as avid a whiskey historian as any here, and you've shared with us many times the knowledge that there are/were many different and distinct recipes/taste profiles. For Maytag to claim his must be 100% rye to be 'authentic' seems to me more like marketing than historical accuracy. So, too, then, I have a hard time truly buying into his claim that he sold his rye young because that was the way it used to be. Again, I figured that as marketing. If he truly believed it, why would he now issue whiskey apparently aged longer? Would that not belie his previous convictions? Was rye/whiskey once sold young? Almost certainly. MUST is have been sold young? Almost certainly not.
The prices for Old Potrero recently dropped somewhat, despite the appeareance that now he's putting out a better, older product. That leads me to conclude: 1) Maytag isn't really committed to a very young, unaged product; and 2) his early bottlings were to raise cash. Now that he has an income flow, he can be choosier about what he releases, and doesn't need to make so much money on it.
On the other hand, I've been wrong before -- probably even already today!