Oubliette the 5th dot of Obfuscate allows a vampire to make people, affected, believe whatever is within the region is real. For example a dilapidated house is a mansion. If you are not within the marked region, do you see the dilapidated house or the mansion? if I'm standing right outside the boundary? viewing with a sniper rifle? satellite imagery?
The power of Oubliette is that it extends the abilities of Touch of Shadow, Cloak of Night, and Familiar Stranger to cover "anyone and anything in his Haven" "at any distance." The marked region demarcates the limits of the Obfuscated property, not the position of the viewer. Whether you are standing within the house, outside the house, or viewing through a sniper's scope, you perceive the what the power's user wants you to see, barring powers such as Auspex or the Clash of Wills.
As per the "Mixed Signals" sidebar, the power "tricks the mind directly," so there's nothing that says it wouldn't work through satellite imagery so long as the power is active. However, as it notes in Touch of Night, showing someone photographic evidence after the fact can bring some memories back, so unless the vampire is constantly using the ability, Google Maps will find you out.