Restaurateurs are actually a far more sophisticated bunch than McClure knows. Decisions about where items are listed, what is bolded, etc. are frequently made with the intent to increase ordering of items with higher margins. The idea that menus are designed without care, or that they a painful source of cost and inefficiency for restaurants, is naive.
"places i visit frequently should give discounts to come back regularly"
Why? If you are already a frequent diner, I have less incentive to give you an outright discount. That said, restaurants frequently reward their most loyal patrons in other ways. If you are a regular and need a last minute reservation on a Friday night, chances are you'll be accommodated if at all possible.
"places i visit infrequently should give discounts to try them once or twice"
Discounting to get customers through the door isn't always a bad idea, but as many less experienced restaurant owners have learned the hard way from services like Groupon, it's difficult to build a profitable customer base by targeting people who are only interested in trying your food because they're saving a buck or two.
"while waiting/eating, i might enjoy music, movies, games, or other media"
There are plenty of restaurants that provide entertainment (live music, televised sports events). If McClure wants someone to baby sit him, however, there are better options than a restaurant.
"First, it would be great if the restaurant knew something about my order history and user profile data, and customized the menu selection to my favorite tastes and interests. Obviously if i’m a vegetarian or a person with special dietary constraints, it would be a high priority to match food options with my specific lifestyle choices or health needs. This would again streamline choice, reduce time & confusion, and increase customer satisfaction. Also, new dishes could be recommended that i might like to try for the first time."
A good restaurant is rarely defined solely by its food. It is defined in part by the experience it offers. A properly-trained waiter is not only more likely to be able to provide satisfactory recommendations, he or she will be able to do so via a human interaction that makes the dining experience more enjoyable.
It seems that McClure's vision for what a restaurant should be is everything that a good restaurant isn't. He's in a rush, doesn't like making decisions, can't do research on his own, wants to minimize interaction with restaurant staff, is afraid to ask questions, prefers external entertainment to the enjoyment that comes from eating a good meal with company, etc. Instead of investing in a space that he appears to know little about, however, I'd simply suggest that he stop by the drive-thru at the nearest McDonald's the next time he's hungry. I think he'll find it to be everything he dreams of, and perhaps it'll even exceed his expectations.