V-belts come in different widths. A too small width will sit low in the pulley and you'll never be able to tighten it enough to get the squealing to stop. You need a belt that sits flush with the top of the pulley, or just slightly above it.
I had this problem with an alternator belt. The store kept selling me the one their computer showed, it squealed, I would tighten the snot out of it, the belt would break, and I'd be back at square one. I finally took the power steering belt in and told them I needed one that thick in the correct length for the alternator. Squealing problem fixed.
Smooth belt vs. teeth is just the manufacturer as far as I know. Shouldn't make any difference as long as you have the correct length and width.
Where is the leak coming from? At the box, you could try snugging the fitting down a bit. At the pump, it's just a hose clamp. Tighten a little more or look to see if the hose clamp has cut into the hose causing the leak.