Most businesses won't take BTC unless it can be easily switched on using their existing POS system. As much as I love buying stuff IRL with bitcoin, at the moment, it doesn't make business sense to spend time learning about Bitcoin, drop cash on a parallel POS system, and train employees, all in an effort to appease a minuscule fraction of their customer base. What needs to happen first is to make Bitcoins easier to comprehend, secure, and use online.
I think you're exaggerating the cost or problems of implementing Bitcoin as a payment system. It would be no harder or difficult than training an employee to use the current chip and pin card devices. 'Contactless' card payments are now being rolled out and I can't see how paying with Bitcoin would be any different from that. In fact, paying with Bitcoin will be cheaper and quicker for the merchant as they don't have to pay creditcard fees etc. Obviously it's still early days for Bitcoin, but the benefits are there to be seen by all and all we need to do is wait for gradual mainstream acceptance which is happening slowly but surely already.
What needs to happen first is to make Bitcoins easier to comprehend, secure, and use online.
That's already happening with payment processors like bitpay. Just give things time. 6 months noone new about bitcoin and you expect for everyone to jump on the wagon already?
Yes, using Bitcoin will become simpler and easier. With every new technology it takes a little while to get used to.