Now here are my concerns. I have NEVER been professionally trained how to ride what so ever. Everything I know has been self taught and things I have picked up along the way of my 12 years riding. How hard is it going to be for me to transition from trail riding in a western saddle my self taught ways, to training to be a jumper in an english saddle with lessons? Shoot, I don't even know where to buy breeches or "tall boots"!
I have contacted two stables near where I am, and both seem friendly so I will go out and check them out and make sure english is something I want to do. Do I show up in jeans and boots? Is that acceptable?
I know the rodeo world and the western riding world is a tight knit community where everyone is friendly and it's a "are you thirsty darlin, want some tea?" kind of people, are english riders as friendly?
I guess my biggest concern is understanding HOW DIFFERENT it will be to put my butt in a pair of breeches and on a type of saddle I've never sat in before and listen to a trainer, with a type of people I have never ridden with before. I consider myself a confident intermediate rider when it comes to what I was doing, but to english riding and wanting to get into the world of jumping, I am a COMPLETE novice! Shoot, I have half a mind to tell the stables to treat me like I've NEVER been on a horse, so I can learn professionally from the ground up!
Am I over thinking this?
This is going to be a huge change for you. The major difference is there is suddenly a LOT less leather between you and the horse. This may or may not be nice. It can be a little starling.. but for the most part you will find your groove :)
Personally check to make sure your boots that you bring are ones you feel happy being in. An english stirrup feels a lot different than a western one.
Jeans are fine, but honestly breeches are so comfortable once you get there. I recently found some jean-inspired breeches for my Western lovin' friend who is learning English with my horse :)
You don't *need* tall boots. Paddock boots are fine, but if you show then some places prefer you have tall boots. I'll be honest.. a good pair of tall boots beats a pair of paddock boots + half chaps. My humble opinion.
As with the world, there are going to be rude people and nice people. It depends on how you approach your lessons. Do not let anyone ever get you down. You know you are experienced.. this is just something new and quite different!
In lessons, there are usually a lot of 'commands' that most instructors bark at you. Don't feel intimidated.. this is their teaching style. Some are more stern than others.
They should, hopefully, have you on the lungeline at some point (hopefully more..) throughout your riding career so that you can get a feel for this new riding style without worrying about the horse.
I'm really happy that you're trying this, though! You're very brave and I'm excited to see how things go!