Definitely get Jobber length bits for most of your drilling, and for sure buy a bunch of bits in whatever sizes you use most often. Also, it's a good idea to stock up on number (not fractional) bits for drilling and tapping with properly sized holes.
There are also two drill bits that have come in big and saved our team on more than one occasion. Keep in the shop and travel with, in addition to regular bits, a few
really long drill bits (usually 12"-16") long in standard sizes (3/16", 1/4", etc). Note, they also come in a
chip-clearing variety that you might like as well. They don't have to be fluted all the way, just enough to drill through a few inches, but they are immensely helpful in drilling holes in hard to reach places. This tool is something that I have used at literally every competition I've attended while working in the pits, and it is something that most people don't think about. You might consider a right-angle drill set to reach difficult places as well.