A primary goal of the Far Ultraviolet Spectroscopic Explorer mission is to understand the origin of the O VI ion in the interstellar medium of the Galaxy and the Magellanic Clouds. Along sight lines to OB-type stars, these interstellar components are usually blended with O VI stellar wind profiles, which frequently vary in shape. In order to assess the effects of this time-dependent blending on measurements of the interstellar O VI lines, we have undertaken a minisurvey of repeated observations toward OB-type stars in the Galaxy and the Large Magellanic Cloud. These sparse time series, which consist of two to three observations separated by intervals ranging from a few days to several months, show that wind variability occurs commonly in O VI (~60% of a sample of 50 stars), as indeed it does in other resonance lines. However, in the interstellar O VI λ1032 region, the O VI λ1038 wind varies only in ~30% of the cases. By examining cases exhibiting large amplitude variations, we conclude that stellar wind variability generally introduces negligible uncertainty for single interstellar O VI components along Galactic lines of sight but can result in substantial errors in measurements of broader components or blends of components like those typically observed toward stars in the Large Magellanic Cloud. Due to possible contamination by discrete absorption components in the stellar O VI line, stars with terminal velocities greater than or equal to the doublet separation (1654 km s^-1) should be treated with care.