Moriah,
I'm sure your head is spinning with all the recomendations, and I'm not sure if it's necessary for me to add to the aleady long list of choices. But, I will anyway.
I know of a very dependable, and excellent carry gun, and they sell for $300 or less. It's the - Bersa .380 CC (Concealed Carry). It has a single stack magazine, has an 8+1 capacity, it's a Double-action - Single action De-cocker, with safety. I have many expensive guns, but I can honestly say this inexpensive Bersa is every bit as reliable Recoil is not harsh either. It works with every kind of ammo I've tried. It's not a "pocket gun". It's compact, although not as small as my Ruger LCP for example, but much easier to shoot, and from my experience, way more reliable.
It fits your criteria, and it'd be an excellent gun for concealed carry if you decide to do that. Normally I recommend small revolvers, but with your desired price range, I think this Bersa would probably fit your needs a little better.
Good luck.