I wasn't too happy about having to buy new lightning adaptors to replace my older 30-pin ones. I did it anyways. It represented a 1-off purchase which did sting a little at the time of purchase (those lightning to VGA adaptors aren't cheap!), but looking back, it's really no big deal considering the years I have held on to it and used it.Good for them. The consumer won't be happy about having to buy new headphones or scruffy 3.5mm adapters which is why it won't happen.
You seem to think this is the first time Apple is introducing a new standard and getting its customers to get more accessories. They are old hands at this and I daresay Apple knows how much they can get away with better than the rest of us.