Princess Auto order arrived and I was able to get my overflow tuned up.
There was a lot of good advise on how to accomplish this because of the previous owners setup , but I came up with the following plan and have great confidence that it will work perfectly when up and running. ( I hope)

Since I have a 1" Drain bulkhead , I will adapt that to a 1 1/2 Drain Pipe inside the overflow box extending up to about 3/4 of the height of the box. With the second hole sized for a 1/2" bulkead, and not really being sufficient for an emergency drain. I decided to break open the new drill bits and bore out the hole to fit a 3/4" bulkhead. Found some adapters locally and second hole will have 1" pipe before and after bulkhead.
And for safety sake, a second 1/2" emergency drain line cut into the back of the overflow, because it was getting pretty tight in there. Thanks to a few of the members for there input on this one.
New bits mean fast drill time, minor chipping and the only real problem I found was that I didn't want to put a lot of pressure on the drill and let it do the work. What I found was that in doing this, the bit tended to sit and bore the hole out rather than drilling a nice straight hole. Nothing serious at all and I am sure after a few more tanks I will get this to work better.
