The present invention is directed to automated apparatuses and methods for measuring fastener hole depth, fastener length, countersink depth and/or hole diameters in a workpiece (or other object) in an automated and extremely rapid, efficient and accurate manner. The apparatuses may be operably connected with a power source and with one or a plurality of computers or other data collection devices to transmit fastener hole depth, countersink depth and/or hole diameter measurement data and/or information to them each time that a fastener hole is measured, while the apparatus is continuously measuring fastener holes (i.e., with no interruptions). Extremely advantageously, using only one hand, and by only squeezing a trigger only one time, an operator of such an apparatus may successfully and very rapidly and accurately perform more than one, or all three, of the following functions: (i) normalize the apparatus relative to one or a plurality of fastener holes and/or workpiece surfaces; (ii) make one or a plurality of accurate measurements; and (iii) transmit the one or more measurements from the apparatus to one or a plurality of computers and/or other data collection devices for, for example, recordation, storage, manipulation, other use and/or the like.