If the budget is $300 than you can not beat the Ruger 10/22 as a first .22 rifle, but semi auto's would not be my first choice for a first rifle to hunt and plink with in the field.
By far the best .22 rifle for a young man would be a nice bolt action magazine fed single action rifle and the Savage MKII is a tack driving accurate and dependable rifle in your budget. My first .22 was a bolt action rifle and perfect for learning safety and hunting. Plus the savage by far would be the most accurate. Maybe even find an old Remington model 41 or 43 Target Master for less than $100.