1. It's the rider, not the board.
There is no best longboard, there is not a best set of wheels, there is no best trucks. There is only what you make of all this equipment that will determine your skill level. You may hear one way or the other, but most of the time it comes down to personal preference.
There is also no best riding style. Freeride, downhill, dancing, carving, slalom, they are all forms of longboarding and they are all fun. One is not better or worse than the other.
2. Picking the right board.
When first picking out a longboard, the different sizes and shapes can be a bit daunting. Here is a quick breakdown.
Longer wheelbases (29 inches+) will give you a nice stable platform to handle higher speeds. Stiffer decks will also handle faster speeds better and give more control in sliding. Lower decks are easier to slide on, while taller decks give you more grip. Decks with noses/tails open up possibilities for freeriding tricks and they also make it easier to pick up the board at a stop. Smaller boards are easier to maneuver but provide overall less stability at speed.
See which one you are comfortable on!
3. Bearing Spacers
One of the more overlooked accessories for longboards, bearing spacers go between both your bearings inside the wheel. They are extremely cheap but the benefits are huge. These things allow you to tighten down your axel nuts all the way, keeping your bearings inline and healthy and allowing for more consistent, less choppy slides.
There are multiple styles of bushings with different shapes made for different purposes. It's always good to ask for help if you are lost in the world of bushings, but I have included a simple guide on bushing shapes and their uses.
5. Be Respectful
Don't be the guy that "The Man" wants to keep off the streets. Respect yourself and your fellow road travelers. That means cars, motorcycles, bicyclists, and anyone else on the road. There is no good to come from adding to our already poor reputation.
6. Get Steezy
There are so many ways to do things, and we are all built differently, so take advantage of your differences and use them to help create your own style. Being different on the hill is just as important as being “steezy” or holding out that slide a little longer. We have this sort of pop-culture type of attraction toward what we think is cool as skaters, but it changes on the regular and you’re never going to keep up with it. The Tyrannosaurus arms things is even getting old! Just do your own thing and do it with a smile.
7. Ease into it
This is especially useful if you are new to longboarding. You are definitely not alone. The first thing you should be doing is riding around as much as possible while gaining balance and control. Falling at 30MPH+ is not going to help you do that. Just about everyone I’ve ever seen ride a skateboard, when they’re brand new and they start bombing hills, takes a big fall off some gnarly wobbles.