The field of very high energy (VHE) ground-based γ-ray astronomy, pioneered by the Whipple 10m atmospheric Cherenkov telescope (ACT) [ 1], is being revolutionized by the second generation observatories, H.E.S.S.[ 2], MAGIC [ 3], and VERITAS [ 4]. Dozens of new γ-ray sources, some representing new classes of VHE emitters, have been discovered during the last decade [ 5]. In space based gamma-ray astronomy a leap in technology from SAS-2/COS-B [ 6,7] to EGRET [ 8] lead to an order of magnitude increase in detected sources; the leap to GLAST/LAT [ 9, 10] technology is anticipated to produce a further order of magnitude increase. The lesson to be learned is that increases in sensitivity, angular resolution and ultimately in scientific output comes through progress in detector technology. In anticipation of such progress it is valuable to re-evaluate the design limitations of current generation ACT observatories and to investigate where improvements can be made that will lead to the next generation. In this paper we focus on one component, the optical system.