I know this is a #firstworldproblem thread but I need help figuring out my setup. There are a lot of different options that I'm thinking about but I'm not really sure what I want to do yet. Right now I have a mid 2012 MacBook Air and an early 2009 iMac. Aside from very simple tasks, the iMac is basically unusable. In contrast, my MacBook Air is still going strong. Finally having a retina display would be awesome though I could very well keep my MacBook Air for another year or so. What I really want is a true desktop experience rather than always looking down at a laptop. I love the larger display of my iMac but because it's so old I can't really do much with it. I've thought about getting a 5K iMac but it's so expensive and I wouldn't be able to use it as a display for anything else (i.e. with my MacBook, PS4, Windows laptop for work, etc.). With a laptop and external monitor combo I would seem to have the best of both worlds. Of course I could keep my MacBook Air and get a 5K iMac but again it just doesn't seem to make much sense since I don't really need two computers. If I opt for purchasing an external monitor, would I want 4K or 1440p? What about one of two monitors and what size? 24" or 27"? What are some good recommendations? What about Dell's U2715H or P2715Q models? Is the new MacBook Pro without TouchBar capable of driving two 4K displays at 60Hz without seriously affecting performance? Is that even be a logical setup? To make things even more confusing I've also thought about switching back to Windows. I've been increasingly interested in information security and software engineering, and based on my limited understanding of these two areas, and the thought of ever going back to school, a Windows machine may be better suited for this purpose along with running Linux as an alternate OS. Is there any truth to this? Regardless, there are a lot of other benefits associated with switching back to Windows. One Windows device that I think is interesting is the Surface Pro 4 but the reviews are mostly mixed and I'm not sure it would be ideal as a primary machine. If I stay with Apple and decide to upgrade from my current MacBook Air, I would probably get either the 13" MacBook Pro without TouchBar or the 13" version with TouchBar. I finally tried the TouchBar tonight and while it seems kind of cool, $1800 also seems like a highly irresponsible purchase for a 13" laptop. I've also heard the criticism levied by some professionals that the lack of dedicated escape and function keys is unacceptable. TL/DR: What should I do? Keep my 2012 MBA and get a 5K iMac? Upgrade to a MBP with or without TouchBar and get one or two external monitors? Switch back to Windows?