Denny, my balancer is sans the crank dogs so it was a none issue. However, it would be easy enough to use a short piece of pipe and a flat washer to give you the clearance you'd need to draw the HB home. As for centering the drill in the crank...my 235's were internally tapered so the drill bit centered itself. I would suggest using a smaller bit for the initial hole....easier to control and makes less work for your 25/64's bit. The installation kit is worth every penny and with the interchangeable tips it's already paid for itself.
I agree totally that it's a wise move to spring for a new balancer. If you've come to love your old balancer (no pun intended) a trip to the Balancer Doctor might be just the ticket. IMO having to change the timing cover seal ($5.00) is one of the biggest PIA fixes on the whole truck. Seems like you have to pull everything mechanical except the tailgate to get room to work!!!! That's why I take the time to wrestle with the timing cover loose, with the seal surface centered on the balancer, and ease it into place. Adding the Felpro Speedi-sleeve to any but a new balancer is SOP. Even a slight weep from the front seal will be blown back over the entire engine and serve as a crud magnet. There's no reason for a 216-261 engine not to be as dry as a bone....even with the down-draft tube.
I wouldn't concern myself too much on the drilling and tapping process. The cranks I've done have drilled like butter and taken a clean thread. I'd make sure that my drill bit was properly sharpened and the tap wasn't high mileage.
It looks like you've set yourself up with a number of operations you can do while she's free of the sheet metal. That's the neat thing about these old Chevy girls; you could put it all back together and drive it tomorrow or spend a month having fun making her fit and perform better than she did when new!!! Ain't old iron great????
Dave