...I also love to go trail riding and it just seems almost sacrilegious to ride the trails in a Kieffer that cost more than my horse did.
If that's the case, then I better find another saddle for all of my horses! I have more money invested in my saddle than I do the purchase of all 3 of my horses put together!!
Money only matters when you're talking about tack. You get what you pay for in tack.
For example, I invested in a saddle that first I am comfortable in, second my horse is comfortable in, and third its built to last forever. It fits one horse with a Classic Equine Sensorflex fleece pad, but I have to ride the other horse with a wither support pad, Classic Equine Biofit, but both horses use the same saddle.
Both chiro (who is also prof saddle fitter) and vet said I was ahead of the game by having more money invested in tack than I do livestock.
It sounds like you are trying to work with your horse to the best of your ablility and listening to him very well. If everything had to "go by the book" then there would be a lot of unhappy people... horses.... dogs..... cars.... Nothing in life truely "goes by the book"!
If the horse is happy, but isn't following "protocol", why worry? Like my dad used to say about raising us kids "they didn't give me a manual, so as long as ya'll weren't breaking laws I didn't see any problem in being a little "unconventional" sometimes...."