Schiit isn't trying to get other people to sell schiit - they're not Herbalife. Schiit wants to sell schiit, which is understandable because it's Schiit's schiit. The resale market generally competes against the direct market manufacturer for sales. If someone is going to buy a Schiit product, choosing to buy it used actually takes a new sale away from the company. So the cost of "driving down the value of the original purchase" only comes from the lowered value of the used item on the aftermarket - which is understandably not something that the manufacturer should be trying to promote.
My reply ... Not completely true, there will be people who at a certain point can't afford a new product, that is reality. However, they can afford second-hand, as when I bought my Gungnir used. Now these people become brand loyal if the product is good, and Schiit is good, really good. So now Schiit has gained a brand loyal customer, that is the GOLD standard in marketing, who cares about a lost sale, the sale was never there to be lost as the person couldn't afford the product new anyway and would likely have moved on to another item, perhaps a less expensive off-shore well featured DAC.
Now the brand loyal customer will expose Schiit gear to their circle of influence, some will perhaps never have considered Schiit otherwise, some will buy new, some used. As well, the original used purchaser may have changed economic fortunes, like myself, and now be able to buy new. I'm a business man, and anyway I can earn a customer, they are my full on customer, lock stock and barrel. Simply looking at some lost margin on a purchase done used is potentially myopic and not really a good business lens. You buy my gear, I value you as you have validated my gear and my business, you're my customer.
Again, Schiit wants to sell schiit. Not an unreasonable position.
Truth be told, the lost resale value is more or less already there though because of Schiit's non-transferable warranties. That's a far larger aftermarket deterrent than the small nominal upgrade fee. Any loss of value from a future possible upgrade fee is going to be negligible compared to the value loss caused by this. I know when I buy used schiit, I weigh the risk/reward ratio of possible future equipment failure against the immediate short-term savings.
The company to some degree already mitigates this "value loss" for the consumer who purchases through them by way of their 15 day trial period. The trial period puts the onus on the consumer to make sure they want the schiit that they are buying. If you think that the schiit is not for you, send it back to Schiit for a near total refund. If you're still using the schiit that you bought from them, then cheaper upgrades actually increase the value of the original purchase to the consumer.
Put another way: In the scenario that you're mentioning (i.e. Someone buys new/used schiit then wants to sell their used schiit to buy wholly new schiit from Schiit but can't because their used schiit has depreciated too much due to Schiit's totally unfair Stalinist warranty and upgrade policies), how is Schiit any different from any other company with non-transferable warranties?
Who knows? Maybe a company will come along that will release products at Schiit's price bracket with same price-to-performance ratio. Maybe that company will provide well differentiated products and a clear upgrade path, with upgrades available even to some prior purchases. Maybe that company will provide transferable warranties to consumers who buy used. Right now, the only company that I can think of that fits these criteria is Garage1217 and they only sell a small line of amplifiers.
When that company comes along, if people want they can take their business there. Free market such and such.