Have you ever taken someone to court?

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I'm trying to decide if I want to pursue legal action against an apartment company I used to live in that violated our contract and cost me a lot of money. I've done all this documentation and spoken to the property owner, but I'm not getting anywhere. He's taking my apartment manager's side of the story and refuses to believe mine. I'm considering going to small claims court, but I don't know anything about it. Have any of you ever taken anyone or gone yourself? Can you tell me what it's like or give me any advice? It seems scary to take someone to court. I don't want to end up with him trying to counter sue me. I can't afford an expensive lawywer, so I'm wondering if I should just give up...and spend my time posting here to try to make up the thousands of dollars he cost me. That could take what, 20+ years?