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 VM

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.