I think that a horse should be for your pleasure and if you're having to overcome fear then that doesn't sound like pleasure - it sounds like stress and anxiety
I know we've talked this round in circles but if you get pleasure out of riding General then buy him - whether or not you keep Obie is down to finances though if you can find the right home for him I would let him go myself - for what you save in boarding costs if the do want a more challenging horse somewhere along the line you can go out and buy one
I so agree, I wish that I had sold Ben before I got hurt, because it just wasn't fun anymore. I should have taken notice when my trainer watched me ride my little fast, looky Arab, and said "You have a great big smile on your face, I don't see that when you ride Ben"
I have had to reconsider my horsey future now, not only did the big guy go, but I am also selling the filly that I bred, that was everything that I wanted, whose Sire and Dam I love, who was to be my last horse. Why am I selling her? Because I really don't enjoy the challenge that she gives me, nothing wrong with her, she is going to be everything that I want, I just no longer enjoy the hassle.
My herd now will be 3 gorgeous Arab mares, one who is retired, and her two daughters who I may or may not ride in the future, but I just enjoy having them around, and Gibbs who will be my go to horse.
Riding should be fun, if you enjoy the challenge, if the ups and downs are fun, then keep Obie, but don't feel you have
to, life is too short, and my thought is there is probably someone else out there for who this horse will be a perfect partner, no shame in admitting that it isn't you, and letting them go.