So, as an update, I've dug deep into my pockets and found a grand total of $1571
For safety I'll include a dash cam front and back.
A nice double din speaker
Some nice new speakers, which should be around $50 from what I can tell, and a safety lock.
This leaves me with around $1200 for the actual car, which isn't bad, right? Plus these things are quality and can follow him to a new car.
I have a friend who flips cars for a living, he said he'd help me find a good one, and when I present him with the list of acceptable cars I compiled from your suggestions, I should have a good one soon. I'll keep you updated, if you are interested. :)
What do you guys think?
EDIT: Also good floor mats