I don't believe people are more cautious or wary of me because I have a shaved head. Certainly older people have made rude comments. I think people of my generation are more understanding as to why one would choose to shave their head. I feel like older people feel like shaving your head is something you're forced to do based on hair-loss where as younger look at it as a choice and that being sly is style within itself.
I'm almost 30 (I became sly when I was 28). When I had hair, I was being asked for ID when I gambled or bought alcohol 50-75% of the time. The moment I became sly, I haven't been asked for ID since.