I ended up with a MacBook Pro because at work we're interacting with a corporate environment for which Linux is not supported and everybody is on Windows. At some point I gave up the fight of configuring a VPN connection to our deeply broken L2TP/IPsec server and asked for a MacBook. My VPN now works, albeit with interruptions.
But my next laptop is going to be a Thinkpad, because these slick MacBooks can't be easily repaired and can't be upgraded. They look and feel good, but that's of no consequence when you suddenly need 16 GB of RAM, or when the battery has worn off, or when the keyboard started to peel. I hate this trend of slim laptops you can't tinker with. OS X is nice, but I prefer Ubuntu's software repositories, though having access to popular applications not available for Linux feels good. And the Retina display on this thing will make all alternatives look inferior.
I also have a Windows corporate environment at work. In your situation I would get a Thinkpad with Windows on it, then run your distro of choice on that with VMWare.
That's what I do on my home machine, because I have 2 mice, 3 monitors and generally with a setup like that, I've found X falls down on its face pretty easily if you start to ask more of it than a basic laptop configuration presents.
Running in a VM I don't have to dual boot (I hate that more than anything) and gain the stuff you may struggle with, such as that VPN connection, with a silky smooth, problem free Linux environment while retaining full support from your company.
I think most of the things you described could be serviced same-day at an Apple store. I haven't been keeping up on them too closely, but I think even the Macbook Pros have soldered RAM and SSD now which is a bummer. A T450 is a pretty good option that's why I've always leaned towards one of those for my next laptop.
I'm a gamer as well so I'm waiting to see how VR pans out before I upgrade again. May stick with upgrading the hardware in my Lian Li tower, or ditching the desktop and moving to a laptop for personal use.
Even better quick fix, install Windows on the Macbook. Then run your distro in a VM on that. :P Not sure why I didn't suggest that. No more VPN issues. When the time comes for a new work laptop, get the Thinkpad and do the same.
But my next laptop is going to be a Thinkpad, because these slick MacBooks can't be easily repaired and can't be upgraded. They look and feel good, but that's of no consequence when you suddenly need 16 GB of RAM, or when the battery has worn off, or when the keyboard started to peel. I hate this trend of slim laptops you can't tinker with. OS X is nice, but I prefer Ubuntu's software repositories, though having access to popular applications not available for Linux feels good. And the Retina display on this thing will make all alternatives look inferior.