Ryan,
Great idea for a thread! I have more drill bits and apparatus than I care to admit. I have a chinese metal lathe and have tons of bits that I use on it, from a full set of Deming bits, a full set of fast relief bits, a full set of TiN numbered, lettered, and fractional all kept in the cabinet the lathe is on with 12 different drill chucks in MT 2, 3 ,and 4.
For wood working I have several sets of Forstner and many, many specialized sized forstner up to 4". I have even bought two sets of the 150 replacement bits ( forgot I had one and bought another), hole saw sets both regular and bi-metal, several spade sets, many step bits, glass bits, masonry, airplane bits (the real long ones), the hardened bits for drilling hardened steel and brad point. I have so many kinds of drills that I have a Kennedy cabinet, center and Craftsman roller bottom just dedicated to drill things. Plus I have several drawers in a low-boy machinist cabinet filled with bits I use for just pens. I love drill stuff.....