My daughter has had a clogged duct since birth and it never cleared, she is now 14 months old and we had the probing surgery 2 days ago. The surgery went really well for her with NO complications!!! Due to her clog she was very nasally and would choke on food and liquids and after every drink she would gasp for air. Immediatley after surgery it was a big difference, now on day 2 post-op, she has not choked or gasped at all. She is doing wonderful and was never phased by the surgery one bit. We will not know if this surgery was a complete sucess until next week when she goes to her follow up appt. As of now I can say I would make the same decision in a heart beat if I had to. If this does not take we will be looking into doing the next step procedure where they insert a catheter and balloon it open wider so it is less likely to close during the healing time. I have heard many horror story from friends who had the surgery done with their children, so I guess it all relates back to how good of a doctor you choose.
To answer your question, if it were me, I would have the surgery done as soon as possible for a much higher percentage of sucess. I wish I would have had her surgery done a lot sooner, but we tried to wait it out for it to fix on its own. As long as you find the best Pediatric Ophlamologist and a great hospital such as Children's your little one will not even know what went on and have great benefits from it. My daughter showed NO sign of any pain or discomfort at all. She was her normal playful self in about 1 -2 hours after surgery (when anethesia wore off). She had no bruising, swelling and (very) minimal blood drainage which is perfectly normal and only lasted about 24 hours. I really hope this helps you, I know how hard the decision is. Good Luck!