[Build Help] First time build, looking to make a nice gaming rig for ~12-1500. Suggestions?

I'm looking to build a good PC that will get me through grad school (Computer Science), and hopefully further. I've done a lot with computers as far a repair, and disassembling/reassembling, but have never built one from scratch. I've been poking around on r/buildapc and other sites, and decided to ask for some suggestions.

Here's what I'm looking for:

• I primarily use my computer for gaming when not working on homework. Ideally I'm looking for something that could run Skyrim at it's highest. I also have (but can't play on my current machine) Metro 2033, which I've heard is hard on a machine. Other than that I play a lot of Paradox Interactive's grand strategy games, which tend to be CPU-intensive (LOTS of movement calculations). I also occasionally host a Minecraft server for some friends, though that kills my current machine.

• I'm aiming for a career in programming/software engineering/whatever you want to call it. Specifically I'm looking into video game programming, though as a hobby or a career I'm not sure yet.

• Related to that, in the courses I'm lining up to take, I'm going to have to do some design work, including 3D modeling and ray tracing. I'd like to be able to work on that on my machine, and have the ability to handle it as a hobby if I find I really like it.

• As a personal point of interest, I'd like to start experimenting with virtual machines, and want to be able to run them on my machine

• I'd really like to run multiple monitors, at least 2, more for multitasking purposes than gaming. Even if I can only afford 1 monitor on the budget, I'd like the ability to support multiple ones in the future.

• I multitask like a madman. 30+ tabs on Chrome, music running, typing away on a bunch of word docs and compiling and debugging 2 or 3 programs at the same time is not at all uncommon for me on a busy day. Even on a slow day, I usually have music, the internet, and some game going at the same time.

• I probably won't be able to build the machine for a while. The money for it will be coming in chunks, so I'll have to get this part here and that part there. This is fine, as I'll be able to carefully watch for sales and such, but I just don't want something that will be useless when I get it all together. My hopeful latest date for assembly is May 2013.

-Related to the above, I'd like to be able to upgrade the machine easily. A few years from now when it starts becoming outdated, I'd like to be able to easily swap out cards/add more memory/replace the CPU (I know that isn't always possible without a mobo replacement, but if it is...), add another card here or there. Basically, I want this machine to last.

• I have a fair sized, and ever growing, media collection, as well as a lot of games. So a lot of disk space is important. I'd like at least 1 TB. I know more than that isn't particularly necessary, but disk space is relatively cheap and I'd rather have it now than need to go buy another drive.

• I would like an SSD, just a small one, to have as my boot drive. 32Gb would be fine, 64 nice, 128 or 256 lovely :). Don't have to though if it would put me over budget.

• I have no personal preference between Intel vs AMD, and ATI vs nVidia, just what ever is the most compatible with the most stuff, and gives the best power for the best value.

• My budget is as such: aiming for ~$1200, would be willing to go up to $1500 if it's a significant advantage, absolutely no more than $1800. That's just for the PC. The project as a whole can't be more than $2000, though the only thing I really need is the monitor(s).

Any recommendations and suggestions are welcome. I'm currently exploring a lot of how-to sites and a lot of the sidebar sites, so I'll update this as I make decisions/learn things, etc. I haven't really looked into the cost of individual components a lot before, especially the motherboard or case, so please bear with me as I learn in that regard.