OlliOlli is a very, very interesting game. It explains exactly what you have to do outright at the start, and even then, I had trouble. That's because I basically had to re-learn everything I knew about skateboarding games.
Without grasping certain concepts, OlliOlli can be pretty brutal, so here's a bit of help.
The first thing you need to remember is that momentum is king. If you're constantly finding yourself slowing down on rails (and thus, falling and ending a run) or losing speed, it's because you're not kicking off enough. Press X occasionally to keep your speed, and remember that there are two "tick levels" that deplete as time goes on -- so to max it out, kick twice.
The second big concept is pressing "X" right before you land. It's very, very easy to forget, and can result in a "sloppy" finish to a trick. You'll need to press it literally right as you're landing, but if you can't get the timing down, try it early so you at least don't get a poor landing.
Likewise, pressing a d-pad direction before you land a grind results in a "perfect" grind. The game teaches you that you can press down to grind, but you can actually press the d-pad in any direction to try out other rail tricks.
In the later levels, you'll want to hold a grind at the end, then leap off. Often times the end of rails or objects have trash heap hazards, and you'll need air to clear them. Busting combos on shorter rails with hazards is a risk-reward process.
Although the game doesn't tell you outright, you can let go of the d-pad while grinding to do another trick, then land another perfect grind and repeat the process. It's risky, but it's a rewarding way to grab massive combos.
While momentum and speed are crucial to your success, you can take it easy every so often to grab the objectives in a level. Most of them are score-based or not reliant on how fast you finish a level, so take your time to slowly grab lots of combos, then speed up after a bunch of rails have passed you by.
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