this time for 30 days! and this time i'm not gonna wear a beanie until it grows back...i want to be bald and i'm a grown man who shouldn't care what other people think of my hair (or lack thereof

)
For me there is no "ought to" or "have to" ... neither should anyone live by the dictates of others opinions. Go with what YOU choose and are comfortable with.
The 30 days is a really helpful time in adjusting and getting used to new routines. Also use that time to try different things with your new routine - find something that works and fits with the way you live.
Strongest reactions are (generally) from family. Friends who've known you find the adjustment hard and often want you to be as they remember you. Those who never knew you before won't bat an eyelid when they meet the sly you.
Know why YOU want to do it, then DO IT. (and enjoy!!).
Well, I guess it's natural to care what people think... and certainly some opinions matter a lot to us.
Like Banmuir said, it's about what you're comfortable with...
I think sly works for you, and would think that others around would think that to. I feel that there's an adjustment period, not just for you, but for your friends too... I have a feeling though that you'll be getting compliments more than anything else
I think you definitely look good sly man!

An trust me I know how it is we always seem to remember the negative comments more than the positive ones, even if we get more positive ones. Not everyone is going to like bald, there are simply to many people in the world with to many different perspectives for that to be true. So just do what feels best to you and everything else will fall into place.