After seeing the comments and doing a quick peruse of my post, I realized that it was a bit rambly and vague. This is probably why other people proofread and edit posts before hitting the publish button, right? I'm terrible at that. I have a thought, I type it out, I hit publish. I'm the same way in person. I have a thought, I open my mouth, I start talking. I'm lucky to be married to a very patient man who knows that talking out loud is my way of thinking. I think that also makes me an extrovert according to some internet tests.
Anyways, here are the few clarifications I want to make.
1. I don't want to get rid of Tessa in favor of the 'perfect' horse. She could be the perfect horse if I would just RIDE MORE OFTEN and DO WHAT I WANT. She's only been on two trail rides and she was not crazy or dangerous or overly spooky on either one of them. If I really want a trail horse, I just need to put some time getting Tessa out on trails. If I want her to learn how to sidepass over poles like a good 4-H pony, I need to teach her how to sidepass over poles. I think the reason I brought up the perfect horse, was to point out that it wasn't the horse. That even if I had the perfect horse who could already do all those things, I don't have the facility/means to do them.
2. Though my barn is an eventing barn, there is no cross country. Everyone trailers out to cross country courses and lately, most of the folks are doing dressage. We don't have pastures to ride in, just large turn out paddocks that aren't suitable for riding around in. Sadly, even the outside of the barn isn't a great place to ride. You can ride around three sides of it, but it's all gravel parking lot stuff except for the trainer's front lawn. I will occasionally ride down the front lawn, but I'm pretty sure they don't want a bunch of horses tearing it up and it's a short line. There are no trails at my barn. Which means the only option I have is to ride in the small indoor arena.
3. There aren't any set 'rules' that you can't ride Western. I actually borrowed a Western saddle and rode Tessa in it. One of my trainers mentioned as I rode by that riding her Western was the fastest way to ruin all her dressage training. Since I have ridden Western before, I disagree with her. I know horses can do multiple jobs and know what you are asking depending on tack and leg and hand cues. But this is a barn that has a program and you're either in the program or you leave the barn.
4. I AM putting off this decision because I love the people at my barn. I have people that I like, people to help me ride the pony if she's too sassy (though this could also be used as a crutch!), people to ride the pony if I can't make it out (again, could be used as a crutch and maybe it would be good for me to not have this to fall back on). My trainers handle scheduling her trims, shots, dental work. They keep track of all of that. They adjust supplements, hay and grain as needed. She might get great care at a different barn, but I doubt that it would include all the extras I'm currently getting.
So....what it seems like the most valid answer is, is to buy a truck and trailer. I am going to look into that option again. But just the storage alone would run me about $100 a month. Then you add in payments for a truck and trailer and the cost goes up even more. I wish there was some sort of 'lease a truck and trailer' program where I could just lease on for a year and see how it goes. :) Anyone know of someone in Washington that wants to lease me a truck and trailer?
Thanks for all of your input and I hope this post is less rambly. Though I still didn't edit or proofread and I'm just about to hit publish....will I never learn?