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Can it show me multiple windows at once or span to a second screen?
I often need to compare two or more files side-by-side, usually in Word. In fact, I've pretty much got my eye on one of those 27-inch ultra-high-resolution displays for just that purpose. But let's give these smaller devices the benefit of the doubt. Could they show multiple windows at once?
64-bit iPad 5: No. But you could use a second iPad.
Surface 2 RT: Yes. In fact, for Word documents, it does this quite well.
Surface 2 Pro: Yes, for all the reasons you can do this in Windows. There is also an HDMI port on the machine that will allow an add-on monitor.
Can it be used to run a development environment?
As a developer, I run a variety of development environments, from PHP IDEs to Visual Studio. Even if the iPad couldn't run Visual Studio (a) because it's a Windows-only product and (b) because the iPad won't support VMs, I'd still give the iPad a nod if it had full PHP development IDEs.
64-bit iPad 5: Yes. As it turns out, there are a few PHP IDEs on the App Store. I'm not sure how pleasant or powerful they are, but I have to give the iPad a nod here, even if it's provisional. It might be doable.
Surface 2 RT: No. Even Microsoft's own Visual Studio won't run on the Surface RT.
Surface 2 Pro: Yes, and quite well. I'd recommend getting the Surface 2 Pro with 8GB (or 4GB at minimum), but it would work quite well.
Image: DraftCode PHP IDE
Can it run Photoshop or Illustrator or Premiere?
I create a ton of presentations and many of them require custom images and vector drawings. I also use Photoshop and Premiere a lot to prepare video from the studio.
64-bit iPad 5: Not quite well enough. The iPad has a wealth of photo manipulation applications and a surprisingly deep stable of video editing apps. That said, getting the precise control you would with a mouse using a finger would be difficult, and the professional Adobe Creative Cloud apps are just not available on an iPad. But with a bulky 64-bit iPad 5, you could probably get by.
Surface 2 RT: No. Once again, not even close.
Surface 2 Pro: Yes, quite well. The peppy Haswell processors in the Pro, combined with full Windows 8.1, a good amount of RAM, and the ability to use external control devices like mice make the Surface Pro a great contender for a mobile media production system.