My mom has had plugs in her tear ducts for over a year now. She has SEVERE dry eye due to what we think was a combination of her Epstein-Barre & getting bit by a tick with a low reading of Rocky Mountain Spotted Fever (like Lymes). Needless to say, she's been to aLOT of doctors because it's hard to pin-point what is causing the dry eye and if it will ever get better. Most likely, the nerve endings and whatever causes your eyes to produce liquid is basically damaged permanently. She receives injections similar to Botox to prevent eye spasms, uses every know possible eye drop & vitamin, & yes, has plugs.
Now to get to your REAL question, lol - she currently has plugs in her eyes and they don't help her very much because she doesn't produce enough liquid in her eyes for the ducts to contain it in her eyes to begin with. However, if your eyes produce enough liquid that it will remain in your eyes with the ducts, it would be very helpful. She has not complained about the procedure hurting once. The first time she got them, she said it felt like they were poking her. Sometimes they even fell out! She discovered that the size of the plug was the issue - you have to make sure the doctor does not put plugs in that are too big for the ducts because you will feel a slight poking (but not painful) sensation, & if they are not the right size (too big or too small), they may fall out.
So overall - no pain, minor issues, helpful if your case is not too severe, & make sure they are the right size. Also, ask him if he thinks you should try eye drops rather than getting the plugs. I know Restastis (spelling?) is supposed to stimulate liquid production in the eyes but can reeeally hurt for the first several weeks/even months that you take it. Maybe another alternative, perhaps a less strong eye drop would do the trick rather than the plugs?
I really hope this helps & that your eyes begin to feel better. Contacts can serious be a beeyotch to your eyes, it's terrible. I worry about that since I've heard/read alot about dry eye bc of my mom. Good luck with EVERYTHING!

eyes are really a delicate thing, which many people do not realize until something happens to them. It's been so hard seeing my mom go through what she is right now, & I really hope that you can find something, whether drops, the plugs, or your eyes healing over time that will make you feel 100% better!! Take care!!