There are lots of socket 1155 boards. If you go on NewEgg and sort by Intel, 1155 socket, then I guess Z77 chipset if you're overclocking. Then with those you can sort by rating or price and narrow it down. You shouldn't have any problem finding a decent enough board around $100-$120. I own
this one. I wish the reviews were a little better on the Z77 boards in that price range but mobos are usually the first thing to blame when something doesn't work, so who knows.
You could use the preview version of Win 8 for free until January. Otherwise, you probably want Windows 7 Home Premium
64-bit OEM.
The various i5s from the last two generations are pretty close at least on the desktop side, but the problem is that their prices are as well. If you live near a MicroCenter there's a good chance you can score a very good deal on one.