My guess is the hole is drilled, you should be able to tell by looking from the piston sode of the case. Some builders plug the hole on the back side to help prevent any leakage that may occure to the the rear. If you are using a non-transbrake balve body the drilling the hole is not needed. I noticed in the pictures that your old case has a 2nd hole drilled for rev feed, again not needed if you have just a manual VB. Your old case appears to be a rear pump case and the is not. If your case is a rear pump your rear pump body will not work on the new case with out a block off plate, or you will need the matching rear support. As far as the pan goes, if the band and clutches are good, then I'm not sure, that is a lot just to be cast iron dust. The band was out of adjustment, if the band is ok check to see if the band adjuster is bent. Something had to have changed for it be that far out.
Hope this helps, Dan