Putting the target on your beam (90/270 degrees) makes best use of your speed to get ahead of him, IF the AOB is <90. It forces him doing al the work in closing to you. And it also means the intercept/meeting point wil be very far ahead. Running at flank so long may not be wise. There may even be islands in the way depending on the geography. If you start behind his beam (AOB >90) and your speed is the same you can certainly forget it, a pointless excercise.
Moving into the 90 degree Dick O'kane setup should only be done at the last moment. You do not want to do that too early or you loose valuable ground on him.
Also, you have to consider how sure you are of it's course. Is it certain to the degree or is it a ENE/WSW kind of course. Those are alot more iffie. You have to figure out how far the convoy can move before you are unable to pick him up on any of your sensors (because his actual course might lead him past your sensor range). Can you get to him before that runs out? That's imho the most important deal-breaker. And the chance he makes a course change before you make sensor-contact.
Have you tried this technique to plot the propper course?
http://www.subsim.com/radioroom/showthread.php?t=88961
Edit: In addition to what the link says: Instead of using the convoy actual position at the time of making the drawing, use the point a safe distance ahead of it to base the drawing on. (place a circle of max visual range on it and let the line to target touch the front side of the circle) This kills 2 birds with one stone. You close on the most efficient course, and get ahead while doing it. Just before crossing his course, do the 90 degree O'kane thing.