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just a bit of advice that i think is necessary
as with skiing, biking, etc etc., longboarding is not about the board, it's about how you ride it.
no amount of money is going to make you a good longboarder. you could buy the best sliding wheels and still suck at sliding, or you could buy the worst sliding wheels and suck at sliding, either way you suck at sliding, and the wheels aren't the problem.
don't blame your equipment, because you'll come off sounding like an arrogant prick unless your deck cracked in half while you were bombing a hill and your wheels exploded into tiny pieces when you slid (both of which will never happen, no matter how bad you think your wheels and your deck are, so suck it up and ride). a sector 9 with a good longboarder on it is better than a loaded with a bad longboarder on it.
don't buy shit you don't need. if you are never going to enter a race in your life, don't buy a racing board, because they're expensive, and they're built for racing, and they aren't worth it unless you're racing, and you'll look like a queer trying (and failing) to have fun on a drop deck on flat ground.
you don't need a helmet or leathers unless you're racing. if you're dumb enough to hit your head when you're not racing then you might want a helmet, but nobody is that dumb. kneepads are great if you're stupid enough to touch your knees to the ground, but don't be that stupid. if you slide, you might want sliding gloves (don't buy them, make them yourself), but they aren't necessary, and you should learn to slide without them before you even bother making them. aside from that, don't be a pussy. you are going to fall and you are going to get some road rash and it is going to hurt, but that's part of longboarding, so suck it up.
if you don't want to get hit by a car, ride against traffic on the shoulder. no need to constantly shoulder check, and you can see the cars that are coming toward you. just don't ride out in front of them and you will be fine.
hills are fun, and easier than they look. it's like skiing, you could go downhill, or you could ski around on flat ground. sure, cross-country skiing is a sport, but nobody gives a shit, and you won't give a shit about your longboard if you never go fast on it. keep your front foot just behind the front trucks and you will never get speed wobbles.
foot-planting is a really stupid-looking, really efficient way to stop or slow down. do not worry about how stupid you look, you already look stupider than you think you do, and you will look really stupid if you don't stop in time because you don't know how to slide.
if you are going fast, you might want sunglasses, but they aren't necessary. i personally had a bee hit my eye at 70k and i spent 15 min picking it's legs out, and it wasn't fun, so just think about that before you decide to bomb the hill with your eyes unprotected.
wear skate shoes if you're going fast. you are going to be very pissed at yourself if you bomb in sneakers and your foot slips.
above all, have fun, and push yourself. none of the other shit i just said matters as long as you're having fun.