How do brands making a video actually calculate the return on investment of all the money they put into trips and whatever else over that time period? Does a video finally drop after a year of filming and immediately their sales rise high enough to cover a year's worth of investment and they can say hey that was all worth it? It all just seems like it would be so difficult to walk away after spending all that money with cold hard numbers as you can't put half of skateboarding 'metrics' like cool factor into your spreadsheet.
I doubt video releases correlate directly to board sales, unless of course you have something like a Limosine model where you drop product and videos simultaneously. Moreso video releases play a major part of the marketing of a brand, making sure its reputation, image, and relevancy is ensured so that income consistently comes in at a sufficient level. For example, brands like Toy machine, Zero, and Alien wouldn't do the numbers they do today without having released their seminal full-lengths. It's kind of a necessary investment for any company in skateboarding; and I bet it's less about how much you spend for a trip than how your spending results in the 'best' video (one that has impact in terms of views and/or legacy).
The issue you bring up is one of running a skate company solely on "cold hard metrics". It's why venture capitalist involvement in skate companies often results in failure. Skateboarding is difficult in this way, as you rightly assume; no MBA can prepare someone adequately for running a skate company.
I think Sci-Fi putting Joa on generates, among other things, a relatively cheap way of marketing the brand. Joa will put out ten videos advertising the brand and its riders inadvertently in the time and resources it takes Jerry to put together one full-length.