No, I don't think there is any real benefit to going with an i7 over an i5 in your case. With the levels of overclocking you're looking for, multipliers aren't going to be an issue.

I don't think that the pin seating issues will cause problems to mildly overclocked systems in the long term, but you never know. If you're worried, the best place to get Tyco sockets seems to be EVGA at this point. Their high-end boards only use Tyco AMP and it's a 50/50 shot with the lower-end boards. You could always return and take the restock fee if you're really worried about it.