Well done, Todd/Josh. You have a new ID as a rising Nashville star, it seems...
You can get a guitar into a drill press without scratching it by taping a diaper onto the drill press table with some masking tape...
From a philosophical standpoint (referring to my old inspiration, "The Nature and Art of Workmanship" by David Pye), any craft project can be typically divided into two types of workmanship: the workmanship of risk, and the workmanship of certainty. An ideally-completed and fully-realized task, whether it be putting a third pickup into a 360, or lathe-turning and hand-carving an elegant wooden bowl (Pye's own specialty), displays a natural balance between these two methodologies. Accepting this balance as a goal, the closer we come to it, the more validity and integrity we will see in the final result. From an emotional standpoint, the final object will be innately more satisfying, both to ourselves and to the observer. It will feel "right".
Artists make much (whether they know it or not) out of violating this ideal; they deal primarily in eliciting emotions from us, whether it be a feeling of being off-balance (with too much tension between the opposites) or a feeling of tranquility (too little tension). So at this point, art and craft take separate roads out of necessity.
The workmanship of risk requires much more manual input (and acquired dexterity) and control than that of certainty, whose characteristics are planning and precision, and which can be done by unskilled and semi-skilled workers if their task is prepared for them.
All philosophy aside for the moment, the feeling of fearful anticipation that we may get when contemplating beginning such a project is a sure indicator that something is out of balance with regard to these two component methods. It could be said that a person is merely scared because he/she doesn't have the skills to accomplish the task (in which case the fear is there for a good reason), but reflection will tell us that this is too simplistic a "solution"...
The feeling of fear is due to a lack of knowledge about the act of fine-tuning the balance between risk and certainty, taking into account (for instance) limited manual dexterity, in which case we skew the approach by adding in more workmanship of certainty. If the fear factor is lack of knowledge about the proper approach or the order in which steps should be taken, then it is incumbent upon the craftsman to avail himself of the immense resources present since the internet came into common use.
In cases of the other side of the continuum, where the cost of certainty (machinery and tooling is expensive) is prohibitive or impractical for just a small task, then it becomes a situation of adjusting the balance in favor of risk, which requires less money (excluding hospital bills for slipped chisels and the like) but much more skill. Solution: practice on scrap.
On the practical side again: Hole saws are for installing locks in doors or for boring bigger holes in thinner materials, where a through-hole is the aim. As Todd "Josh" Bradshaw has stated, a Forstner bit clears away the wood inside the circle as well. Anyone who's had the guard off a Rick bass (especially a lefty) knows the distinctive look of a Forstner-rendered hole.
Todd's 100% correct (nothing like experience coupled with awareness and great communication skills to make one an exceptional teacher) in this: if your gut feeling is hesitation at attacking the surface of a gorgeous two-pickup Rick in order to install #3, try installing a pickup on a plank using the same method you plan on using. Success in this will help with the confidence problem, and it's confident craftsmen who do the best work. (Over-confident tradesmen do lousy work--that's why I had to re-install my kitchen faucets...the plumber put 'em in backwards while trying to impress with his abilities, then left behind a great pipe wrench that I had to call him to pick up later...)
Oh, and the difference between "tradesman" and "craftsman"? Well, "tradesmen" show up late, leave early and have lots of reasons why things are not as simple as they seem. Oh, and there's the bill, too.
Craftsman, on the other hand, is a brand of tools sold by Sears, Roebuck, and Company.