I had hair down to my collar a little bit over a year ago. I have two cowlicks as well, which makes shaving the spots a pain, but I also have a shadow. When I shaved it about 2 weeks ago it was 70s and sunny. March decided it hates me and now it is 30s and 40s and gloomy out.
I shaved at 11:45am, it's now 2:15pm. I can feel my stubble, though when I was shaving and a bit after you could put a baby's bottom and my head in a blind test and not be able to tell the difference. I do remember though, when I first did the shave I was very self-conscious of it. The difference between how random people treat you is a pretty cool flip. People in general seem more cautious around me now that I don't have hair, they're more likely to hold a door open, move out of your way in the bars, etc, and they're also more receptive of you doing the same for them.
So in a nutshell, being bald is fun, while having hair is...well having hair.