I think it's great how you described the idea of 'console age groups'. It had never occurred to me.
I never really thought of Steve Jobs as a tech ambassador, either. As for why people disliked his company, I feel there are other reasons. While the cynic in me agrees that it was because people felt his products were 'mainstream', there are other reasons. Many people felt like Jobs was selling flashy, overpriced tech that had superior alternatives and pandering to novice users who wouldn't know the difference.
The explanation is similar with indie culture. Many people feel that the motivation of mainstream media, be it film or games, is to sell tried and tested ideas rather than experiment or branch out. Thus, these people will eventually lose interest altogther.
Ultimately, the frustration with the mainstream isn't just an obsession with hating all things popular. It's more like people think a concept is getting way too popular and it doesn't deserve the attention. So there is a legitimate beef to be had with mainstream culture.
Having said that, I think your advice is excellent. Often, an item's mainstream status will cloud someone's vision. I think we should just ask if it's good or not.
I for one am a reformed Apple hater. For me what changed was realizing that I had never really looked at the products - I sort of joined a bandwagon. I still have criticisms - but I try to divide my criticisms of their products with my criticisms of their mass appeal. In fact, I embrace Apple because they really have become gaming's greatest evangelist.
Now my problem is the opposite: I mind game enthusiasts who feel that people who play iOS games aren't worthy of the 'gamer' title. I think it's important for the labels associated with video games to completely fall away, and I think game fans should spread the word after they've dealt with their own misconceptions.