I'll try to keep this short as I can-
I've been riding at the same barn for about 4-5 years. Last summer, I got my first horse (I'd leased before then) and I've boarded him at this barn since then. It's a small 'backyard barn' style barn, and $500/ month is inclusive of feeding, stalls for inclement weather...the basics. The barn and everything are in pretty shabby condition, but it's not too bad. And there is an small arena and jumps available. I've been riding with a trainer about once every other week as well, but the problem is that I'm not sure she's as experienced with hunter jumpers as she's led the people at the barn to believe. Don't get me wrong, she's a really great trainer, but I think her expertise is in areas like paint shows and western pleasure. I don't really like the headset that she has my horse working in, and I feel like she's pushing me more toward paint shows when personally I'd rather do hunter jumpers.
Anyway, my sister was trying to sell her horse at the beginning of summer (she's going to college and can't take her), and one person that came to see her was from a pretty fancy show barn in the area, for their lesson program. My family was going on a month long vacation, so long story short, my horse ended up going with this lady to the fancy show barn for the month to work in their lesson program as well. They're not paying me and I'm not paying them, so I'm pretty pleased with how it worked out.
HOWEVER, after seeing the facility... I'm really wanting to start boarding at this new barn. It's really nice, PLUS they go to a lot of shows and are equipped to transport horses (that was a constant problem at my old barn).
Here's the problems with switching to that barn though-
1. The board is $1000, which includes 4 lessons a month as well. This is the most glaring problem, but I feel like there's a pretty good chance we could make an agreement for him to be used in lessons 3 days of the week, and for me the other 3, in exchange for the board to be dropped to $500. If it turns out this wouldn't work, this move isn't something I'd even consider- but for the purpose of answering this question, let's pretend that they do agree to it. ;)
2. I don't want to break relations with anyone at the current barn. There is another horse whose owner is paying me commission to sell him, and he'll be staying at the barn where I'll continue riding him. I really don't want it to be awkward when I see my old trainer or barn manager around the barn. They're currently pretty low on horses as it is, so I don't think they'd like me too much if I took my horse away too. I also need my barn manager for work references, since I've worked there for several years and she's my go-to person for references or recommendation letters. Plus I would like to keep my job there!
So there, hopefully that wasn't tooooo confusing. I guess the problem is that I feel like my horse and I could be more competitive at the barn where he's staying right now- but I wouldn't be able to ride him as much and it might make things weird with the people at my current barn. Please let me know what you guys think, it would be enormously helpful!