Lot's of good stuff here.
To see what "ordinary lifestyle advertising might look like one only has to peruse the old Raleigh type adverts from the 50's in England. Normal people using normal bikes for normal activities. The Clubman was the bike you could ride to work all week and with friends on the weekend and most utility bikes had all those things (guards etc...) you described.

I do think the Citibike / bike share concept comes close to ordinary people using bikes for day to day activities but one very attractive aspect of that is that people don't have to worry about what to do with the bikes. That model completely eliminates the security/parking aspect of using a bike. That's a huge benefit.

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Advertisers don't want to sell products - they have to sell products; and more specifically their products. That's how they pay the bills and make money. Spending a lot to creating advertising that only shows the product in the background in a generic sense opens the door to the target market thinking the brand of bike itself doesn't matter. Lifestyle brands, like Surly or Rivendell (sorry to keep bringing them up but they are great examples) create a lot of peripheral lifestyle with their blogs and accessories but they still highly emphasize the benefits of their particular brand of bike and they are kept central to the theme.