The technology is simple enough. It definitely creates more infrastructure to maintain, but simple enough. Every restaurant and shop could have a validation machine. Customer remembers to ask them to validate the ticket received on garage entry. On exit, it waives the fee, or discounts it, or waives a few hours, whatever.
Operationally, that's a lot of machines to spread around, to places that don't really care about them. Along with rules and enforcement about how those places use the machines. Otherwise, it's not long before one of them just puts it out it in the open for self service. Or, there's just one out in the open instead of at each establishment. Now that it's self service, it's easy for anyone to use, even if they don't buy something. Even buying something, how much is enough? If you buy a sundae and nothing else, is that good for 12 hours of parking then? Do you need to spend a certain amount of money first before you can validate? All these little things start to add up. They are easily worked around to get cheaper parking while at the same time making the desired customers mad instead.
This is really the entire question. Is DS designed and used to support "mostly resort guests and a few locals/off site guests" or is it "mostly locals/off site guests and a few resort guests"? Which of those groups spends more money at DS and supports the entire ecosystem there?
If it's the first scenario, charge away for parking and discourage locals/off site guests.
But, I suspect that resort guests alone cannot keep DS profitable, that it's the second scenario. Where locals/off site guests are the primary DS customers, drawing them in and it's not primarily onsite resort guests keeping DS profitable. This model suggests that parking should be free to entice more use. Free and easy to use, draw people in, primarily competing with other outside establishments and not with in park/resort ones.