The Transiting Exoplanet Survey Satellite (TESS, launched early 2018) is expected to find a multitude of new transiting planet candidates around the nearest and brightest stars. Timely high-precision follow-up observations from the ground are essential in confirming and further characterizing the planet candidates that TESS will find. However, achieving extreme photometric precisions from the ground is challenging, as ground-based telescopes are subject to numerous deleterious atmospheric effects. Beam-shaping diffusers are emerging as a low-cost technology to achieve hitherto unachievable differential photometric precisions from the ground. These diffusers mold the focal plane image of a star into a broad and stable top-hat shape, minimizing photometric errors due to non-uniform pixel response, atmospheric seeing effects, imperfect guiding, and telescope-induced variable aberrations seen in defocusing. In this paper, we expand on our previous work (Stefansson et al. 2017; Stefansson et al. 2018), providing a further detailed discussion of key guidelines when sizing a diffuser for use on a telescope. Furthermore, we present our open source Python package iDiffuse which can calculate the expected PSF size of a diffuser in a telescope system, along with its expected on-sky diffuser-assisted photometric precision for a host star of a given magnitude. We use iDiffuse to show that most (∼80%) of the planet hosts that TESS will find will be scintillation limited in transit observations from the ground. Although iDiffuse has primarily been developed to plan challenging transit observations using the diffuser on the ARCTIC imager on the ARC 3.5m Telescope at Apache Point observatory, iDiffuse is modular and can be easily extended to calculate the expected diffuser-assisted photometric precisions on other telescopes.