Overall, things look very nice. You have the good grades in both your Bachelors and Masters, you have good long work experience, and worthy and plausible goals, that I feel would be very interesting for the Adcom, especially if you were to show how much potential this business has for growth. Although Asian, being from SE Asia is an advantage as majority of Asian candidates are coming from China or India.
I feel like you have made a good choice of schools for family entrepreneurship. The schools you listed make perfect sense. Since you are in education/tech you might also add Haas and Stanford to that list, maybe Yale as well. And I think that would be a good start. The list is a bit on the tough side, I admit, but if you can make all these applications in R1, that will give you enough leeway to tweak your strategy moving forward.
As for applying R3.. I dunno.. it is really hard for International applicants, and it drops your chances a lot. If it is REALLY better for you, then you can take your shot... although, in your specific case, if you would be happy to go to INSEAD, what you might do is right now work on your INSEAD app for the January intake, and if you get in, go. And if not then apply R1 for the rest.
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