Hi umbucker. Import some music at a higher bit rate that you have at 196kbps and see if you can hear a difference. I feel that once over 320kbps it is hard to tell. That is based on my own experience and the 46.86% of headphone lisrteners who have taken part in a poll on another forum. In the same poll only 1.42% of respondants were happy with 196kbps. The poll has 479 replies. So to B the answer is that you would probably not be wasting your time, but check first.
I have not heard the IE Bose, but the on ear cans are very good in a dynamic bass driven way. So to A I would say buy with confidence and ignore the usual anti-Bose sentiment. Lifestyle packages and speakers for shops mean Bose do not have a great audiophile reputation.