The more comments I read the more i think maybe its a cultural thing 
A lot of horses around here are pushed to the end of their scope even if they aren’t the most confident because, at least from what I’ve heard from other trainers, you should always "aprovechar’ the whole horse until he can’t jump any higher.
Honestly i believe that’s like a really bad thing to believe but I think I myself might be thinking that way without meaning to. But yet again you guys are 100% right
No comment on the health issues as you have already gotten some great advice here.
I will say that in my experience, if I am asking myself if I should sell a horse, the answer is generally yes.
I briefly leased a small horse (15.1ish?) to do the jumpers on, and we ended up having similar issues on the related distances. Her stride was too short to do the numbers, and she was not fit enough to rock back consistently to add a stride and jump comfortably from there. In the end the horse was not a good enough match for me to want to put in the time to work on getting her fit and comfortable being ridden rocked back down the lines. No shame in deciding to find a better match for both yourself and for the horse 
Good luck!
I think there is definitely a cultural difference between the US and every other country with horse sports. Here in the States we have our strengths and weaknesses, as do all countries. We definitely tend to be less aggressive and softer in our ride, which I think comes from the hunter/equitation foundation so many of us get. It took me YEARS to learn how to gallop in the jumper ring when I started doing that, and even longer to learn how to actually sit my solid little WB to the jumps (which is what he prefers), and not do a nice, light, pretty half-seat constantly! 
I have known a few people from Latin America and to a person their riding style tends to be more forward and aggressive, and their horses reflect that in the way they go. Some horses and some riders do really well with that, and sometimes it starts to fall apart, especially when the jumps go up.
If you find it more fun to not be catapulting toward the jumps you should absolutely feel confident in telling that to your trainer and looking for a horse that suits you better. It sounds like you have been really successful with your little guy, so finding a good next home for him with someone who wants to win at the lower levels is a good idea and hopefully won’t be too difficult.
Thank you for clarifying.
If the money from the sale of this horse will enable you to get a better horse, don’t waste another day in frustraton. When you are riding your new horse, provided you choose wisely, you will be so much happier…and safer!
If however, the money from the sale won’t improve your lot, save up. Stop spending money on shows and get yourself a better horse. Life is too short to stay in any type of relationship that brings you down. Let him be someone else’s problem.
Best of luck to you. Let us know what you decided.
Riding should be fun.
Fun for the horse and rider (and trainer and parents if everyone has the right mindset).
It doesn’t sound like this partnership is fun for you or your horse. And those two things are the most important. Full stop.
Sell this guy as a lower jumper. Test ride a lot of horses until you find one that clicks and you feel excited about riding again.
Sell the horse. In the interim, stop doing things on him that don’t turn out well. If that means you practice flat work, or technical courses of small jumps, so be it. A good trainer can give an incredibly challenging lesson where the rider improves over cross-rails.
So I have decided not to go back and I’ve kept his for sale ad up, now all I can do is wait for someone to offer to buy him. I’ve had plenty of people ride him and enjoy him but sadly none have sent me a message or called me to let me know they want him. Hopefully he sells soon so I can bring Fin home before anyone else gets wind of him. Thank you everyone for your kind advice!
Yeah, I already have a really nice guy in mind. Posted a thread on here recently asking for advice between to horses I was considering and I finally landed on a pretty solid WB, really sweet temperament, and from what my trainer has said he can probably help me get up to the 1.30 if I continue to move up in my riding
Update: Someone tried him out yesterday and loved him! Little girl who’s looking for a fast ride, can do diagonals like a pro, is ready for the 90 and 1.0m, and quick jump offs with agility, which checks all of my little guy’s boxes, and even when he did run out on one of the jumps she still really enjoyed him! Hopefully she’ll decide to keep him so I can bring Fin home as soon as possible 
I’ll keep you guys updated
Awesome! I hope it works out!
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