That's another thing Legacy changed/misinterpreted from the original. Kevin Flynn didn't want information to be free and open-source. Just the opposite -- he wanted to reclaim his stolen intellectual property and the enormous profits from it that should've been his all along. Sure, in-story he wanted programs to be "free," but in the sense that he wanted them to be controlled by their individual programmers rather than taken by the company. This was before ubiquitous personal computing, after all, so computers and programs were mainly in the hands of people who worked as programmers, not in the hands of the general public. So Flynn's mission, and Tron's parallel/allegorical mission, wasn't about open-source software versus copyrighted/for-sale software, but about labor versus management, about individual creators being entitled to control and profit from their own creations rather than having to surrender them to their employers. (A theme that I believe had some resonance to the filmmakers working within the Disney corporate empire.) Flynn's goal was for himself and the other programmers to have the right to make money from their own work. So when his son in Legacy made Encom's newest software available to everyone for free, thus depriving its developers of income, he wasn't standing up for Kevin Flynn's ideals, but betraying them.
that's was Kevin's 1982
philosophy...by within a few years, he already had plenty of money, and was working on his own little world. And didn't the ISO's appear BEFORE he got trapped? If so, by that time (and when Sam was old enough to comprehend stories), Kevin's attitude toward money might have changed.
At that point, money was nice, but not the end all (as opposed to livin large CEO of 1983).
And certainly Sam had lived his whole life WITH lots o money, and saw how meaningless it was (which led him to his daredevil liestyle..which to me, really made his "action hero" stunts in the Grid believable to me). i think Daddy Flynn would understand, especially if it seemed lke the Corporate attitude had come back into power (as it apparently had; Sam had controlling interest, but a typical Corporate exec ran the day-to-day, and in effect EnCom as the "true" CEO)
So by 1992,
Sam was taught a certain philosophy of life, and the 2010
Sam probaby was indeed going the way his father intended (adjustng for the fact that Dad was gone during even more formative years of high school and college).