I appreciate everyone's input on this. I am very primitive when it comes to drills/drill bits, taps, etc. I have just about every nice hand tool imaginable to work on the Cummins. Done just about every bolt on/bolt off job to the engine, but for some reason I am very intimidated (scared) with this. I'd love to just slap the manifold back on and be done with it. But with future plans of a neighborhood of 100psi of boost, I better do it right.
Here's what I've done so far. Started a hole, I'm up to a 5/32" drill bit/hole. Unfortunately, I'm off center, slightly to the bottom of dead center. The next step up in drill bits I own is DULL. Yeah yeah, take my butt down to the parts house. When I jump up to a bigger bit, it starts cutting into the head. Since the hole is off center

So I tried a 5/32" extractor, well I guess you need a small tap wrench to turn it, cause my primitive drill just spins on the extractor that is 'stuck' in the head. I'm sure this is elementary stuff to many of ya, but I never done anything like this. I really don't want to screw up this new head. I think I'm gonna pull it again

, take it to a shop and let them deal with it, cause I don't have the tooling to do it right, without screwing up something.
Guess I'll just stick to governor spring installs, injection pump R&R, clutch, heater core jobs etc, and leave the 3rd grade stuff to the pro's

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Last question. I've already torqued the head down. Do I need a new headgasket when I R&R the head again?