Why is pretty easy....every time you come up with a "Disney should" idea pretend you are a manager at Disney trying to sell the idea to Senior Management. Answer these questions - how much will this cost to implement? How much to maintain? How much will this cost us in lost revenue? How much will this gain us in revenue? What is the margin on the revenue we will gain and loose? Disney is a corporation, as such, its purpose is to make money. You won't have the answers to these questions, but you can take some guesses. If you can't add revenue in excess of cost, your idea will get shut down.
For instance - Magical Express. That has got to be a pretty expensive program to "give away for free" - but Disney now has their hotel guests "stranded" on property. They can charge more for restaurants. Sell more dining plans. They don't share their revenue stream with Sea World or Universal. Guests staying a week on property frequently end up adding "pluses" to their tickets. Plus, they can add the cost of the "free" service into hotel room costs where the rack rate is much higher than for similar hotels off property. In the end, it really ends up "costing" Disney very little (and they further control their costs by contracting out the service), but has a significant revenue add.
Some things - like free internet for
DVC members cost Disney very little to run - but giving up the revenue stream from the hotel side for the internet access at this point might be a bigger deal. Or it might not be. If it isn't, then Disney will eventually just give it away.