Hi D.
I had my umbilical hernia repaired when my son was 8 months old. I had the surgery 1 month after the hernia appeared and was diagnosed by my primary care doctor. I had it done at Northwestern by Dr. Eric Hungness. He is young (probably late 30s) but experienced and I was very happy with him and his nurse.
It was a one day, outpatient procedure. I went in early morning, had surgery, spent about 1-2 hours in the recovery room and then came home. The recovery was easier than I expected. I have had 2 c-sections and those were definitely harder recoveries. I did not even need to take the prescription pain medication that they gave me to go home with. I did have mesh placed to repair the hole, but no complications thankfully. I did try to get some help with my kids as you are not supposed to lift anything heavy for a couple of weeks but we managed with friends/family and some additional help. It's doable (I had 3 year old twins and an 8 month old at the time!)
You will need surgery at some point. The danger in waiting and seeing (and I am not trying to scare you) is that the hernia can become strangulated. Literally a portion of the intestines/internal organs can get trapped in the open muscle, and that is a life threatening medical emergency (which actually happened to my mother-in-law, it's very serious). I personally would not even think about going through another pregnancy with an unrepaired hernia. I don't think anyone can guarentee that you will never need surgery again, but you're definitely better off having it repaired.
I do have a little "smiley face" incision over my belly button. It is quite small and very thin and faint. I'd even be willing to email you a picture of it if you would like to see Dr. Hungness' work! ;)
So yes, if it were me, I would get it repaired soon, recover, and then get pregnant. HTH!
**edited to add, based on other responses, it sounds like most doctors advise waiting until after pregnancy but you might want to contact Dr. Hungness for a second opinion**