I found that my problem was unclear instruction about the timing between jumping and popping. One day when I was watching a slowmo ollie video though, I noticed that the skateboarder already was beginning to jump (at least his body was already going in an upward motion) before snapping the board off the ground. That was a critical change I needed to make in order to get it working. I had been trying to pop the board while all my weight was still pushing down on it (kind of an obvious mistake, but I somehow overlooked this). Hope this helps somebody.
It is mainly because those items are guaranteed to help you familiarize yourself with the ins and outs of using them. They are a big help in making you feel comfortable when you push off with your feet while also balancing on top of the board when riding. It is not good to go for a very technical product, so it’s best to choose the mentioned types first.
This can be tricky to figure out, so just take your time and relax. The first few times you try and ollie, it helps to not worry about this part. You will end up doing a sort of half-ollie, popping just a little in the air. Or, you might fall! But, don't worry, this is all part of learning. If you want though, you can certainly start with rolling your ankle when you try and ollie - whatever works for you! Eventually, you will need to roll and drag, and you'll figure it out. Just take your time!

Rails (or ribs), are narrow strips of plastic or metal that are attached under the deck lengthwise along the edges. They are used for additional grip for grabs, and to enhance sliding while protecting the deck's graphics at the same time. Rails also provide a more consistent feel for slides, as the slide of a regular skateboard will suffer from the wear of the paint or varnish on the bottom of the board. Although rarely used anymore, they are useful for experienced skaters that are capable of grabs.
It is mainly because those items are guaranteed to help you familiarize yourself with the ins and outs of using them. They are a big help in making you feel comfortable when you push off with your feet while also balancing on top of the board when riding. It is not good to go for a very technical product, so it’s best to choose the mentioned types first. 
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