I actually have two horses. My first horse, Baloo, a pinto Arab cross. He was 19 I think when I sold him, and I had to make the choice between selling him, and getting a younger jumping horse, or keeping him, and sticking to flat cause we couldn't afford to have 3 horses. I opted to sell him because I really wanted to continue jumping, and he could no longer jump, and I know that he went to a great home, but I still wish that I could have kept him.
The second is my Thoroughbred mare. I had her for 3 years, she had a lot of minor injuries, and two big ones, all of which amounted to a whole lot of vet bills over the 3 years, and after my dad's horse died, he said I had to start paying for her, and I just didn't have the money, so I had to sell her. The first person I sold her to had her for a couple of years, then had to sell her due to lack of time, and having a young child, and found out horses was just too much, and she ended up calling me up, and giving me the option of buying her back, but I didn't have the money, and I had my 3 year old gelding, so I had to pass. Knowing now that shortly after that call, I had to put my gelding down anyways, I wish that I had actually seriously thought about it, and pulled some finances together to buy her back, but last I heard she's in a great place, and the guy is absolutely in love with her. She's his best trail horse, and he's already refused several offers for her from what I've heard, so she's got a home for life. I would have loved to see how far I could go with her in the show ring.