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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.

Learn how to ollie off of a ramp: Ramps are a LOT of fun to ollie off of, but they are also a great way to break something if you don't know what you're doing! I have a cousin who almost lost his arm because of how nastily he broke it while ollying off a ramp. But don't let that scare you - if you know what you're doing, ollying off ramps is great!

It wouldn’t be until the early 1980’s however, that a man named Rodney Mullen fully developed the skateboard ollie and brought it into vogue. Competing in the Rusty Harris contest in Whittier, California in 1982, Rodney Mullen used a back and forth motion on his skateboard to strike the back end of the board on the ground and using the front end to level the board out in mid-air – all from a flat surface. The audience’s jaws collectively hit the ground.

Cruiser - The name says it all. If you are looking to cruise around town then this is the right complete skateboard for you. These decks vary in length from between 20 inches all the way up to about 40 inches. The wheel diameters usually start at about 55 millimeters and use a much softer urethane than the previous Popsicle decks. These also come with all of the above but the decks do not always need grip tape. Some of the decks are plastic or composite material with grooves or gripping built directly into the deck mold. 
Slide your front foot as soon as you start jumping. Use the same movement you have been practicing to slide your foot towards the top end of the board, just as you jump off it and kick the back down. The front of your board should lift up as you slide your foot along it, with your foot hitting the top of the board at the highest point of your jump.[9]

The wheels of a skateboard are usually made of polyurethane, and come in many different sizes and shapes to suit different types of skating. Larger diameters (55–85 mm) roll faster, and move more easily over cracks in pavement and are better for transition skateboarding. Smaller diameters (48–54 mm) keep the board closer to the ground, require less force to accelerate and produce a lower center of gravity which allows for a better response time, but also make for a slower top speed and are better for street skateboarding. Wheels also are available in a variety of hardnesses usually measured on the Shore durometer "A" scale. Again like car tires, wheels range from the very soft (about Shore A 75) to the very hard (about Shore A 101). As the A scale stops at 100, any wheels labeled 101A or higher are harder, but do not use the appropriate durometer scale. Some wheel manufacturers now use the "B" or "D" scales, which have a larger and more accurate range of hardness. Modern street skaters prefer medium-sized wheels (usually 51–54 mm), as small wheels with lighter trucks can make tricks like kickflips and other flip tricks easier by keeping the center of gravity of the skateboard closer to the deck, thus making the deck easier to spin. Street wheels are harder (A 100/A 101). Vertical ramp or "vert" skating requires larger wheels (usually 55–65 mm), as it involves higher speeds. Vert wheels are also usually slightly softer (A 98/ A 99), allowing them to maintain high speed on ramps without sliding. Slalom skating requires even larger wheels (60–75 mm) to sustain the highest speeds possible. They also need to be soft and have better grip to make the tight and frequent turns in slalom racing. Even larger wheels are used in longboarding and downhill skateboarding. Sizes range from 65 mm to 100 mm. These extreme sizes of wheels almost always have cores of hard plastic that can be made thinner and lighter than a solid polyurethane wheel. They are often used by skateboard videographers as well, as the large soft wheels allow for smooth and easy movement over any terrain.

Unlike some deck options, which are completely bare, the Bamboo Skateboards Galaxy Series Cosmic Cloud Skateboard Deck features heat-stamped artwork on the underside of the board, including several geometric and interstellar designs, including a beautiful nebula. Bamboo Skateboards claims these boards last their customers three weeks longer than other decks. The company sells the boards in three sizes: 7.75-by-31.5-inches, 8-by-31.75-inches and 8.25-by-32-inches.
The longboard, a common variant of the skateboard, is used for higher speed and rough surface boarding, and they are much more expensive. "Old school" boards (those made in the 1970s–80s or modern boards that mimic their shape) are generally wider and often have only one kicktail. Variants of the 1970s often have little or no concavity, whereas 1980s models have deeper concavities and steeper kicktails.[7]
Ohderii Skate Skateboards are made of a High-quality Plastic deck which will not easily break even when pressed over by a car.  It comes with 3.125″ all aluminum alloy trucks, 59mm 78A super smooth PU wheels and ABEC-7 stainless steel bearings.  It is ready to use and you can easily store it in your backpack.  It has an average rating of 4.5 on Amazon.