I don't necessarily consider myself excessively computer savvy (insofar as really understanding the underlying architectures of computers), but I was in somewhat of a similar situation before I purchased my own gaming rig this past summer. My advice...
1. From your posts (no offense), I gather that you are somewhat leery of assembling your own computer. My guess is that since you likely haven't built a computer before, you don't really want to be responsible for putting the whole thing together and picking compatible parts and the like. I was in a similar situation. I ended up buying a fully assembled computer from an online retailer.
Note: this company was more geared towards gaming computers than dell will be. I live in Canada, and bought mine from NCIX.com. I could definitely have saved a bit by pricematching carefully and picking up deals, but dealing with one retailer, and having an included warranty is a nice bonus. In my case, this has allowed me to transition into owning a desktop and working with its insides. I've overclocked my CPU, swapped out RAM (had to do a bit of troubleshooting), installed wireless card, etc. This isn't complicated at all, but since I don't have any friends who habitually build gaming computers, I didn't want to dive in without anyone to pull me out if anything went wrong.
tldr: if you aren't comfortable building a rig all by yourself (though most people say it is actually quite easy), check out some retailers that specialize in gaming rigs. why?
a) Dells or other similar companies build computers for non-gaming, internet-surfing consumers. This means they will skimp in certain areas in order to save money (why put in parts that your customers won't use and cost you more?) These areas include
i)graphics card (GPU): this is REALLY IMPORTANT because your GPU is a huge part of your gaming performance. Graphics cards don't matter for people who only surf the internet, so the graphics cards Dell provides are lower-middle class at best. Sure, they may be able to play Skyrim, but not maxed, or with graphics mods. And 2 years down the line, you won't be able to run games any more. This means you will either have to purchase a new graphics card NOW, or have to upgrade your computer a few years later, which wouldn't be an issue, except for...
ii) The power Supply (PSU). Companies like Dell use weak power supplies along with their mediocre graphics cards. It doesn't make sense to stick a powerful PSU into a computer that doesn't draw much power. This becomes an issue if you want to get a better graphics card (which requires more wattage). The 350-450 watt Dell PSU just can't power these cards, so upgrading just got a whole lot more expensive.
iii) the case: Companies like Dell use their own cases. They are of decent (but not great) quality, and are obviously intended for non-gamers. This means sticking in a big graphics card often WONT FIT. Your upgrade path is hampered if you don't consider it from the start.
tldr (real): Buying a computer that isn't intended for gamers can work, but it will never be optimal, and in the long run, you will end up having to pay extra to cover your traces. You are better to get a computer designed for what you are doing. Though Alienwares do have good specifications, they cost more than they should. You get a good computer, but pay too much for it, so you are better off getting the same computer at a lower cost elsewhere.
2. Look up component reviews and get acclimatized with available parts. Hate to say this, but life is a lot easier if you know approximately what parts are available, and how they stack up. What is the consensus processor? what GPUs seem to perform well for the money? Are new, better parts coming out within a month? This takes a bit of work, but is well worth it. Sites like Tom's Hardware, Anandtech, etc. Benchmark sites can show you how things perform. Better still, sites like Tom's often have articles suggesting computer builds at different price points. You can model your choice off of their recommendations.
3. Figure out your requirements and expectations. Do you expect to upgrade a part every year or so? Keep the computer the same way for 5 years before buying a completely new one? This may change what you want to buy. If you are OK with upgrading, it doesn't make sense to overpay now for top of the line components when you can upgrade in a year or two and get the same performance for half the cost. However, if you want the computer to last without modification(always difficult), you may need to splurge a bit. Typically, there are sweet spots in price/performance. For example, the 2500k processor performs fantastically (along with large overclocking headroom), and costs significantly less than the 2600k. Anything over those processors was overkill. Many websites show price/performance graphs and give recommendations.
4. For Skyrim:
a) processor: Skyrim isn't too taxing on the processor in MOST cases. The exception to this is in certain areas which seem to stress a single core quite heavily. For this reason, places like Dragonsreach and Markarth give almost everyone large framerate drops. The best solution to this problem is to have a CPU with a high clockspeed. For example, I have a 2500k at 4.1 GHz. This is a minor overclock for the 2500k, but has been shown to help. In 95% of the cases, though, Skyrim won't really tax modern gaming CPUs. However, you want to get a good processor because it is likely a part that you won't want to upgrade for a while.

RAM: memory won't really be too much of an issue. Almost all computers sold now come with around 8 GB. I would try to stick to 8 GB or so. 4 GB will suffice, but at your price point there is no reason to cut corners here. 16 GB is excessive in almost all cases.
c) Graphics card: Skyrim on its own isn't incredibly demanding, but mods can bring down the best of machines. Especially when it comes to high rez textures, graphics power is essential. One of my only regrets with my rig is that my SLI 560 ti's have only 1 GB VRAM. This is fine for the vanilla game, but high resolution textures use a ton of VRAM. I would suggest going for something around 1.5-2 GBs to be safe here. VRAM isn't the only factor by any means, so check some benchmarks. the 6950 2 GB seems a solid choice, or the 560 ti 2 GB, but you should also look at the release date for the next generation Nvidia (Kepler I think), and that of AMD.
d) Storage: There is a shortage of hard drives at the moment due to a natural disaster in Thailand. This means hard drives are currently more expensive than they have been for a while. You may have to skimp on capacity and speed in the meantime. You should also consider whether you want to include an SSD in your rig. SSDs perform very well as boot drives (for your operating system), and for launching programs. They are incredibly fast, but this speed is offset by their high cost per gigabyte. For this reason, many gamers build new rigs with a lower capacity SSD, along with a larger (but slower) storage drive. This allows for fast speed, along with more storage space. For Skyrim, any drive will suffice. SSDs will decrease load times, but will have little to no effect on frame rate.
5. My Rig and What You can Learn: I bought my rig for games like Skyrim, BF3, Arkham City, and the like. My budget was slightly higher (around 1700 canadian), but could be brought lower depending on choices. The specs and reasons are as follows
MOBO: MSI p67 (forget model offhand): works with my 2500k, not much to say.
CPU: intel 2500k (overclocked to 4.1 ghz): This is a great processor, the consensus choice for a while. Still probably the best value.
RAM: 8 GB Mushkin ddr3 (dual channel): This is another no-brainer. For the most part, RAM doesn't really influence too much in the way of gaming performance. Just don't undershoot too much, or go way overboard needlessly.
GPU: 2x 560 ti in SLI : This is the controversial part. Buying 2 mid range cards has both advantages and disadvantages. My 560 ti's perform better than the top of the line 580 for the same price, but there are upsides and downsides.
upsides: more performance for the dollar, SLI scaling is much better now than ever before, if you want go the multi-monitor route, you need at least 2 cards (if using nvidia).
downsides: scaling is great for some games, bad for others. In general, older games scale worse in SLI. This normally isn't a problem, as older games are less demanding, but games like modded Oblivion may not perform as well in SLI as with an equivalent single card. Also, SLI performance often improves with new drivers, but these drivers are not always released promptly. SLI can also give headaches occasionally, so single cards require less troubleshooting. Buying a powerful single card now also allows you to buy another down the line to improve performance. However, this usually isn't practical because new cards have come out, so it makes more sense to buy more recent models than to SLI an obsolete card.
Note: one thing I regret is getting cards with 1 GB of VRAM. Though 1 GB is sufficient for most games now, maxing out BF3 will use over 1 GB VRAM, and modded Skyrim also uses a lot of VRAM. Though my cards are powerful, I may run into increasing amounts of problems later on when consistently hitting my vram cap.
Storage: 2x 1 TB Caviar Black : I bought these drives when they were cheaper, and did so specifically because I record footage using fraps. I run my OS and games off one drive, while recording to the other. The default configuration was an SSD boot drive and a large storage drive. This second option would likely be better for your needs.
I apologize for the giant post. It took a while to write, but I hope it helps with a couple things. Don't be scared and buy a bestbuy computer ill-suited to your needs only to regret it later. Research a bit, and everything will be fine. If you have any questions, there are tons of people willing to help. Don't take their word as gospel, but many people are willing to help.