overseas shipping & scam prevention

hello

im using paypal for the first time to send $645 CAD to an individual in canada. im in the U.S so it will be converted. because this is my first time, (and im weary i wont recieve my package), how can i make sure i dont get scammed?

if i do get scammed, does filing a dispute really work? i almost lost $900 on another site sending money and i cannot do that again.

sorry if this is a dumb question. thanks for the help