No, he's far from being out of touch. You have to consider that Gary and WotC are coming from two totally different points of view. The d20 STL is based on the belief that the most "popular" RPG is the best RPG. From reading his replies to those questions, its not much of an assumption to gather that Gary believes that the best game would have the best quality rules and supplements and be easy to introduce to new gamers. WotC put a plan into action to sell more PHBs and let other people produce what they will. As far as the OGL/D20 is concerned, there are no other provisions--nothing about attracting new players, nothing about improving D&D, nothing about quality (although there are some standards now)--nothing except selling more PHBs and increasing D&D's "popularity".
Frankly, some of the questions are just plain loaded. How could products produced under the OGL improve D&D? (I'm assuming that "improve" means to somehow "make the rules better.") Nothing produced by a party using the d20/OGL is "official", so the core rule books remain unchanged. (What happens at the individual gaming table being up to the participants.) How could the OGL attract new players? Unless a 3rd party put out an introductory set, which couldn't be d20 and stand alone at the same time so it would have to be OGL and then the connection with D&D would be lost because the d20 trademark couldn't be used.
I don't think Gary's out of touch, so much as the questions don't make any sense.