Hey Wingz, thanks for joining SBG! Your questions are all valid, but they've been asked by thousands of men before you. The answer is and always will be - SHAVE IT FOR 30 DAYS STRAIGHT!!! Within a few days, hours, min of shaving you'll know you did the right thing!
Tyler says it well here.
I'll say Welcome, but I want to say more.
To minimize the radical change from hair to sly, gradually run your clippers shorter and short. #3 for a week or two, EVERY DAY. (so it looks stable at that length). Then #2 for a week or two every day (it only takes a couple minutes to do this ... less than the time it takes to shave it bald). Then #1 for a week or two and then take the guard off for a week or two. You may speed the process up be decreasing the 'week or two'.
My clippers have a variable length between settings so I took it in 1/3 increments. And for about 3-4 days each.
Then when I was down to no guard for a few days ... took the razor to it and shaved bald. Many people seemed to not notice. took the immediate family that I live with three days to notice the change!
There IS a big change between buzzed no guard and bald. Bald is SLICK, shiny, smooth, feels excellent. Wear it proudly.
And Oh, as you are going shorter and shorter with your hair, look around you for the other bald guys. You'll probably see that there really are a lot of them. I'm not talking about those with the horseshoe or some hair left is strange places. I'm talking about shaved completely bald on top.
Personal opinion, a bald head looks great with a beard.