2 different scenarios here. This one's for work, and they did pay for it, but who pays doesn't matter if it's for making money in one way or another. In work situations, cost of computers are not material compared to the cost of employees. It's an investment in the employee, and you get whatever makes them happy. You can cheap out and force cheaper PC's or something else, but it'll just send a bad signal about what your company is about.
For personal use, my last MBP in 09 has lasted me to this day. I didn't use for work, so I didn't use it every day like my new one, but still. I've never had a PC laptop come close to that longevity. I don't mind paying extra for quality builds or superior every day usability. It makes every task a little easier. Everyone has experienced IT hell and troubleshooting stupid s**t. The less of that happening makes everyone happier. Not saying this doesn't happen with Mac's, but given my experience, I'll take my chances with Apple. No need to justify anything in my mind. I'll pay for quality every time.
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Very good point - like I want the touch bar MBP but would be willing to get the nTB because of the cost.. I probably will end up kicking myself later.
I don't know if you'll be kicking yourself between the tb and ntb. I think the other benefits of the 16 are more impactful (but touchID and 4 ports is nice). I would kick myself for going 2015, but that's just me.