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Not sure the area you are in, what type of riding you do, or if you replace show clothes periodically. Growing up we always went to the Goodwill stores and picked up blazers to show halter and showmanship in. Normally for under $5 a jacket. If we wanted something flashy we would go to the craft store pay $1 or $2 for a bag of sequins and sew them on ourselves. We could even find boots, riding shirts, and jackets that we could use for english at times. Pants were also easy to find at Goodwill, also under $5 a pair (these are current prices at the Goodwills near us, I think they were $3 when we were growing up).
As for shows, we would look for shows with payback classes or that gave prizes (bags of feed, buckets, spray bottles, etc). We went to one show that was rained out after 4 classes, my sister and I happened to have gone in 3 of the classes that ran, and won all three of them, so we left with over $100. Another show we left with 7 50lb bags of feed and some money. This year my niece showed in a few classes at a show and left with $55, and this was her first year ever showing.
Typically halter and showmanship are the classes you can easily win the most money back in. My sister won a high-point earlier this year at one show, won a few odd and end prizes as well as a $50 gas card, so things like that really help.
If you are showing dressage or jumping, I'm not sure if there is any way to make some of the money back. I don't think they offer pay back classes at those, but I've never been.
A friend of ours was married to a farrier that worked at some of the hunter barns, he was always bringing stuff home that they were throwing away. Tack that was used too much for them to use the next year, blankets, halters, etc. Heck he even had some horses given to him from time to time (and this was long before the downturn in the horse market). So maybe you can do some part-time work at one of these farms, and get some stuff that way that you can use later.
Also, as far as buying a horse, there are many people that are giving horses away right now, and others looking for people to free lease horses from them for the time being. Maybe they don't want to sell the horse, but can't afford to keep it boarded somewhere right now that would be willing to work with you.
Another possibility would be to talk to some breeders in your area that may have some young horses that they haven't been able to sell, you could ride and show them, and they may work a deal with you so that if you sell the horse for them you get a commission, then you could work with another horse they have. I know we looked at doing something like that with some we had in the past that needed refresher courses, and we didn't have the time to do it. But if we could have found someone willing to ride the horse for us, we would have gladly given part of the sales price to the person.
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