Upgrading Current Build

Memory prices are always dropping.
I remember when I bought my good and old Pentium and paid $30 per megabyte...
As of your up-grades, it all depends on your current experience.
I mean, I have a Crucial SSD myself, and couldn't be happier with it. If you really get annoyed waiting for your system to boot, or your programs to load, then go for it.
When it comes to memory, it's like you said. Prices are down, and 8Gb is the sweet spot today. If you have a 64 bit OS, why not?

My w/ my current setup I have everything on the 500gb. No partitions for the system drive or anything like I should have. The boot times are fine, Windows loads in 20 seconds. I have heard that w/ enough RAM, games can be ran strictly off the RAM rather than relying much on the hard drive speed. Is there any truth to this?

Also as far as memory goes, I know that failure rates are still fairly high compared to other components, but are there any brands that are better than another or is it all personal opinion. Also, I plan on sticking w/ 1600 GHz, the PC12800 I believe. Is there a noticable difference between timings? Mine is 9-9-9-24 now, How much more should I pay for 7-7-7-24?

Thanks

After further thinking, I will likely buy 16g of the RAM listed and remove the 2 slots I currently use. That would cost 160ish or I will add 2 additional sticks of the same RAM I have in for 8mb total for around $50.

1) A ram upgrade is a good idea, here is some added justification:
http://blog.corsair.com/?p=65

2) Ram is sold in kits for a reason.
Ram from the same vendor and part number can be made up of differing manufacturing components over time.
Some motherboards can be very sensitive to this.
It is better to get what you need in one kit.

3) The Intel current cpu's are largely insensitive to ram speeds or timings. Don't pay much more for faster speeds or better timings. You can detect the difference with synthetic benchmarks, but you will be hard pressed to tell the difference in application performance or FPS. Fancy heat spreaders are mostly for marketing, don't pay extra there either. They might be good for a record seeking overclocker only. Tall spreaders may also get in the way of your cpu cooler.

4) All SSD's perform remarkably similar doing the things a normal desktop user does. Don't make a decision on glowing synthetic benchmarks that bear no resemblance to what you will use a SSD for. Today, I think Intel 320 or 510 are the SSD's to get. Their track record for reliability has been better.
http://www.behardware.com/articles/810-6/components-ret...

http://www.newegg.com/Product/Product.aspx?Item=N82E168...

I believe that I am sold on this upgrade, will likely wait on SSD upgrade.

That seems like a complete steal to me, I was actually close to paying the full price on tigerdirect.com