Large-format (sub)millimeter wavelength imaging arrays are best operated in scanning observing modes rather than traditional position-switched (chopped) modes. The choice of observing mode is critical for isolating source signals from various types of noise interference, especially for ground-based instrumentation operating under a bright atmosphere. Ideal observing strategies can combat 1/f noise, resist instrumental defects, sensitively recover emission on large scales, and provide an even field coverage - all under feasible requirements of telescope movement. This work aims to guide the design of observing patterns that maximize scientific returns. It also compares some of the popular choices of observing modes for (sub)millimeter imaging, such as random, Lissajous, billiard, spiral, On-The-Fly (OTF), DREAM, chopped and stare patterns. Many of the conclusions are also applicable other imaging applications and imaging in one dimension (e.g. spectroscopic observations).