Choices from my own experience and all bought for well below your price limit:
Tokarev (Norinco makes 'em in 9MM, too!)
Old Colt police revolver in .38 SPL
An old S&W K-frame in .38 SPL
Star Mod 30
Personally, I like Toks and the Norinco Tok in 9MM is one killer pistol. It's target-gun accurate and it hasn't jammed on me once. For something more powerful, get a 7.62 pistol; Wolf makes a great 7.62 hollow point.
These things are great shooters and seem to go cheaply. I picked up a good one for $250 this year.
Maks and K-frames:
They're great but I'll let others fill you in with the details.
If you splurge $15 on a softer hammer spring and a stiffer recoil spring from Wolff, this becomes a great, easy-handling, very accurate gun. The DA pull becomes very pleasant. It also has never jammed on me.
Star Mod 30:
DA/SA, 9MM, built like a tank, accurate, easy to strip down and the mags hold 15 or 17 (Ramline's 17 round S&W 5900 series mags work in this gun!) Never a jam with this one, either. I see them in like-new condition on Gunbroker for $350. Mine cost $235, I think.
Here's the Star in case you're not familiar: