Does small claims and garnishment really work?

I have roommates who skipped out on me, stole from me, and left me with a pile of debt. I will be claiming for ~$500 in damages (more than $500 costs more to file). My case is clear cut and I will win (he signed a lease with me and notorized it), but from what everyone tells me about small claims it dosn’t work, people don’t pay, I’m screwed, etc. Once I get my judgment how likely is a motion for garnishment to work? The motion costs an additional $185 + $40 service fee (which will be tacked onto the judgment). This guy works a tax paying job, is not a head of a household, and does not have kids. Do judges usually grant garnishment motions.

I could kick his ass but I don’t want to. I just want my money back