goodroi - 7:25 pm on Jul 22, 2013 (gmt 0)
Yes, Google is fine with multiple websites owned by the same person. Google actually owns multiple websites in the same industry (for example google.com/videos & youtube.com, or orkut.com & plus.google.com)
Google wants to see a good experience for their users. If someone searches on Google and gets bad results they stop using Google. As long as the websites each provide their own value, there is no problem.
Is it possible that sometimes the multiple sites will be spam? Yes and those sites run a higher risk of being penalized. They aren't being penalized for being owned by the same company. They are being penalized for not providing value/good experience for searchers.