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Can it be used to grade my classes?
I teach an object-oriented programming course at UC Berkeley extension and we use the ANGEL learning management system. ANGEL requires the availability of both Flash and Java, as well as — in some places — Windows media.
64-bit iPad 5: No way. iOS does not support Flash or Java.
Surface 2 RT: No, although not necessarily well. Surface RT originally only whitelisted a few sites for Flash, but now just blacklists those sites it doesn't trust. But it doesn't run Java.
Surface 2 Pro: Yep. It's Windows on Intel.
Can it be used to run virtual machines?
I use virtual machines a lot. Before Windows 8 Pro, my go-to VM was VirtualBox, but I'm doing more and more with the built-in Hyper-V now. In either case, though, I need to run VMs.
Because I teach programming, students have to program. They're all using Visual Studio, but some use Visual Studio 2010, some 2012, and some are tinkering with VS2013. Each version of Visual Studio lives in its own virtual machine.
I also run VMs for testing questionable software and I run a number of Linux VMs to stage my websites before uploading them to servers. Additionally, I field a VM for whatever interesting new virtual appliance or application comes my way that I don't want to test on my main machine.
Now, before I put the three machines to the test, note that I'm not talking about hidden VMs that come as part of provided solutions. I'm talking about the ability to spin up my own VM and run it, with whatever OS inside I choose.
64-bit iPad 5: This is where a 64-bit iPad gets interesting, because you might be able to support a lot of RAM. That said, it's unlikely we'll see iPads that come with 8, 16, or 32GB of RAM that will let you run three or four VMs at once. In fact, the iPad doesn't have a way (other than remotely connecting to a real desktop) of supporting VMs at all.
Surface 2 RT: No. No good news here at all.
Surface 2 Pro: Yes. This supports Windows 8.1 Pro, and that includes native HyperV support. You can also run VirtualBox if you want. You can order a Surface 2 Pro with as much as 8GB, so you can quite nicely run a VM or two. My current laptop has 32GB, but while that's nice, the Surface 2 Pro would do nicely.
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.