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You don't need to jump to the 5000 series - but I would at least go with an HD4850, it's around $120 now, and plays everything just fine.
Since you are going to be using somewhat demanding programs, and you're using a 64bit OS, I would definitely go with 4GB of RAM. If it weren't as cheap as it is, I wouldn't recommend it
As far as upgradeability - you're already choosing a platform that is being replaced. So, upgrades will really only be video cards and maybe more RAM, and hard drive space. I don't think anything new is coming out for the LGA775 socket, everything is moving to LGA1366 and DDR3.
You might as well buy a decent heatsink now, and get the OEM version of the processor (it just won't come with a heatsink). Games aren't going to need an overclocked E8400 for a long time, it'll be much more dependent on the video card. Except for GTA4, but that doesn't count, because it barely runs on anything out there without a patch.
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