As for not enough blood coming out, what works best for me (after the making sure your hands are warm etc) is to prick, and then put the thumb of your other hand in your palm, grabbing your hand, and move the thumb towards the finger you've just pricked. That way you're pushing the blood up to the tip. If you just squeeze the tip you're cutting off the blood from below the tip.
Another thing coming to mind is, are you sure you're holding the right part of your teststrip to the blood drop? It really needs only a very small drop, but it needs to go into the top end, between the flat layers, so not on the flat part of the test strip.