Unless you've got insurance that'll cover it, and/or cash money for fairly serious injuries, you probably shouldn't. You won't bounce back like most of us did in our childhood and teens, and you stand a chance of seriously fucking yourself up.

Depending on where you live, sidewalk construction may be an issue. E.g., paved areas in the UK can be shitty due to inconsistent height between paving stones. The slightest thing and the newb is gonna go flying.

The thing to remember with skateboarding is that for every several minute video showing cool tricks, you aren't seeing the hours of bails. The Tony Hawk games always included bails videos to show that there's a lot of perseverance and pain that goes into making it look effortless.

I did myself some horrible injuries over the years, including slashing the palm of my hand wide open on a pebble-dashed wall whilst learning just to coast. Also gave myself a horrendous groin injury at one point whilst casually riding around.