Due to their violent stellar winds, ionising radiation and famous deaths as supernovae, massive stars play a key role in galactic evolution. A complete understanding of these objects has been hindered by both their rarity and by the relatively limited volume of the Universe that is accessible with existing facilities. Addressing the first of these limiting factors, the VLT-FLAMES Tarantula Survey (VFTS) has drawn from the 30 Doradus region an unprecedented sample of over 800 O and B-type stars. The survey is beginning to uncover a wide range of global properties such as the region’s binary fraction of massive stars and their dynamics, whilst also looking in detail at some of its more fascinating objects. This thesis documents the reduction of the VFTS data set, whilst also describing the analysis for one of the serendipitous discoveries: the massive binary R139. This high-mass binary will provide an excellent future calibration point for stellar models, in part as it seems to defy certain expectations about its evolution. Outwith the VFTS, a search for binary companions around a trio of B-type supergiants is presented. These stars are surrounded by nebulae that closely resemble the triple-ring structure associated with the poorly-understood SN1987A. Do these stars share a similar evolutionary fate? While strong evidence is found for periodic pulsations in one of the stars, there appears to be no indication of a short-period binary companion suggested in the literature. Gathering observations from a wide range of environments builds a fuller picture of massive stars, but the samples remain somewhat limited. The coming generation of extremely large telescopes will open new regions for studies like the VFTS. Fully utilising these remarkable telescopes will require many new technologies, and this thesis presents one such development project. For adaptive-optics corrected, multi-object instruments it will be necessary to position small pick-off mirrors in the telescope’s focal plane to select the sub-fields on the sky. This could be most efficiently achieved if the mirrors were self-propelled, which has led to a miniature robot project called MAPS - the Micro Autonomous Positioning System. A number of robots have been built with a footprint of only 30 x 30mm. These wirelessly-controlled robots draw their power from the floor on which they operate and have shown the potential to be positioned to an accuracy of tens of microns. This thesis details much of the early design work and testing of the robots, and also the development of the camera imaging system used to determine the position of the robots. The MAPS project is ongoing and a number of the potential future tests, and avenues for new research, are discussed. This is a thesis that brings together an area of active astronomical research with cutting-edge technological development, highlighting how tomorrow’s telescopes will be an essential tool to answer some of today’s most puzzling research questions