While Bob might have slightly better chances of lucid dreaming due to his low stress and laid-back lifestyle, without as much structure. You also started that he enjoys the simple things in life and observing the world around him. (Reality Checking.) However, if he is constantly stimulated, he might have less mental energy at the end of the day, and without such a structured life, he is much more willing to accept a new or unusual scenario as normal.
Brian might find more difficulties with a stressful life, but if he is constantly doing repetitive work, then he might have more mental energy at the end of the day in order to practice lucid dreaming, assuming he has time. With a repetitive lifestyle, he might be more likely to take a new or unusual scenario into question (when it might be a dream.) Also, with the stressful lifestyle might come lack of sleep, large quantities of caffeine or alcohol, all of which can be a detriment to lucid dreaming.
The truth is I don't think the life you live has too much of an impact on lucid dreaming, as both lifestyles you mentioned above seem to have their own benefits and drawbacks. Also, these lifestyles are somewhat unrealistic. Everyone is going to be somewhere on the spectrum in-between these, having aspects of both a structured and stressful working life and a stimulating and dynamic social life.
I firmly believe so long as you maintain a positive attitude, consistent sleep schedule and practice regularly, you will be able to lucid dream no matter what your lifestyle is.
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