I forgot about protection, thanks for raising awareness Frosty! Absolutely wear a helmet. Most of the time when you fall on a rail, you hit your head. Hard enough to if you're not wearing a helmet, its going to hurt bad, but if you are, it shouldn't really hurt at all.

Like Frosty said, we're not trying to scare you. This is just precaution for worst case. It just needs to be said. If you respect the slopes and the terrain park, it will respect you.

Now to the fun bits. Practice. Anywhere that has snow, is grounds for practicing anything. A lot of us are spoiled with ample snowfall to where we say "lift ticket, pfftttttt" and just ride the trees all day long. I see you're from North Carolina. I actually learned how to snowboard in Maggie Valley at Cataloochee. So I'm aware of how sometimes finding snow can be a problem. But thankfully from this awesome winter, you should have snow around in your yard. If you have a hill, shovel it into a line and make a track to do a run. If no yard snow, drive up one of the mountains in NC and spot a backcountry line. Or fill a truck up with snow. One thing I remember from being raised in the south and being a snowboarder, is being creative. We used to use skateparks as mountains. A bowl for skateboarding became a concrete halfpipe for snowboarding.

If you're looking for something to mimic a rail and have ample snowfall, an old snowboard works great. The base of a snowboard and the top of a rail are fairly similar. They're just different enough to where you do not get friction riding across them, but both are nylon based. But with a snowboard being not that incredibly long, it wouldn't have enough time to gather the friction to hang you up. So being close to Sugar Mountain, you should be able to find an old busted up snowboard for pretty cheap. I picked one up at a garage sale over the summer for $15. Makes an excellent beginner rail. But honestly, any table like surface should work just fine.

As far as teaching an ollie. This is almost impossible to tell someone how to do. I can show you some dynamics to try to get your brain to wrap around some of the physics involved, but outright telling you just will not work. So try this to learn what exactly is going on in your snowboards mind:

On a carpeted surface, do a tail press. If you do not know what this is, strap in as usual and lean back over the tail as far as you can safely, and pick your front foot up. You should notice the nose of your board raising off the ground. This is an exaggerated version of the 1st part of the ollie dynamic. Getting your board under load for the pop.
2nd, when in your tail press, jump up on your back foot. Try to land with the board completely flat on the ground. That is the 2nd part of the ollie dynamic. The release of tension in your board, and the leveling out for the landing.

Now if you tried this off of a jump in a terrain park, you would wake up minutes later to find out you just threw your first backflip or if you're off balance, rodeo, and failed. So don't try this on the snow in person. Its just a learning example. But it can get you to notice the double action of "loading up" and "snapping."

A true ollie is like a hop, but staggered. Basically you are going to pick up your front foot first, and hop with your back foot + all of the added tension of your snowboard under stress. Now you see why I can't teach you this, its something you have to figure out. Timing. And trust me on this, trying to learn an ollie on a snowboard while moving is NOTHING like trying to learn an ollie while moving on a skateboard. It's a bit harder on a snowboard. I don't know why, but it is. If you truly want to master the ollie, and you're riding the mountain, find some little bumps or baby jumps that are usually littered around the sides of the trails near the trees. Or small kickers in the beginner terrain park. That is the best way to learn, to pop off a lip. The ramp is there to help you. The flat ground will not at all.

It sounds as if you're just coming into your own as a "freestylist." Now is an exciting time of snowboarding. Finding out what you can do, and finding out what you want to learn to do. Try everything. When it comes to box riding, maybe a boardslide is easier than a 50-50 for you. So try it. If its grabs, maybe mutes are not your thing, but indy is. Now is the time to try. And if you fail, try again! For me, frontside anythings are a nightmare. Can't do them. Doesn't mean I don't try.  But backsides (which everyone considers harder), I can land as if it was natural.

So find yours. Find whats easy for you and master it while dialing in on the things that are difficult. There is a ton of weird things you're about to learn about your skills while pushing yourself beyond the "mountain riding" barrier. I found out I can only ride in the woods switch. Who knew? Its little quirks like that which make snowboarding fun. That and riding with friends. Yes thats sappy, but its true.

And please keep coming at us with questions. Sometimes I forget how lucky I am living in a snow zone and knowing what I know until I get to share the knowledge with others.