...Even if the missile/ramming ship has a speed advantage, I don't think that alone isn't enough to guarantee that you can make hi-speed contact. (If speed at impact in not a concern, then yes, I think [2] is probably true.)
It is obviously easier to chase a slower target down from behind, (though your energy on impact will be substantially less) than trying to intercept head on. (If you have enough time, you can turn around and try again if you miss.)
I think we need to remember that even a relatively low speed contact can carry a heck of a lot of energy when talking about ships instead of missiles. Even if we're talking about a little 10 dTon fighter, if we assume the average 10:1 figure then we have around a hundred metric tons of mass impacting the target hull. If you did nothing but coast beside him and then give a 1 second 1 G burst, that'd still be a 5 million joule impact. Now think about catching up from behind with only that 1G difference and and only one standard thousand second or 20 minute turn of thrust behind it: that hundred tons of mass is colliding at speeds measured in kilometers per second, and impact energy is measured in kilotons.