If ddr2 is what you already have, then yes, this upgrade will work. But newegg has had similar deals on newer phenom II x4 cpus with board which may overclock better. Check their daily deals and combo specials, or register for email promos. The tiger direct combo doesn't come with a heatsink or three year warranty, so it's only average.
Yes, it will work. But you have to ask yourself if your game will benefit from the extra cores. Your old board will work with some 95w phenom II's at half the price. The newer 1055t series is only available overseas right now and works with a bios update on your current board; it's also 95 watts.
the game i play is quite processor intensive as it runs alot of scripts for collisions and navigation. so i might benefit. my other question is would it be worth it to buy it for the long haul scenario? considering that the tech changes often would it be worth it to buy it as an investment to allow me to not require an upgrade for a few years as opposed to when the next big thing comes out?
At that price point, I would look at Sandy bridge instead, with a cheap motherboard. I use the h55 series for my i3. Sandy bridge is worth the money; the six core amd's are ok but for the long haul I would look elsewhere. You say you're not upgrading, but replacing the board and cpu is an upgrade. IF you want to spend $271, then at least sell off your old stuff first. If you don't get any decent offers, then consider the 95w phenom II instead. And there's no such thing as an investment for computer stuff. It's changing so fast now that "future proofing" is a waste of money.
The cheapest Sandy Bridge cpu will be discounted by Microcenter and available starting on 1/9/11 for $149.99 (in stores only). Boards start at about the same price. I don't have a microcenter in my town, but frys may offer a similar deal.