Dear Anything,
I am a huge advocate for child-led weaning, so that part of your post was difficult for me. However, I can totally respect where you are coming from and applaud you on your year of nursing -- it's so much more than many accomplish.
That said, I would contact your local La Leche League league leader to discuss your concerns about your dental work and mole removals -- I am not positive, but I think there are ways that these can be handled in a breastfeeding-friendly way. I'd also seek further information on the breast reduction. If you plan to nurse again, I'd be VERY careful. I am going to do some more research on this as well and post what I find in links or perhaps an article, and LLL might be useful here for you as well.
In answer to your question, even though we did wean child-led, my first daughter needed a little push to stop the actual ACT or nursing before nap and bedtime (our last one as well) even when it was clear she wasn't getting any actual milk during those times. I am a staunch opponent of cry-it-out, so for me, the answer was Daddy. Not that there weren't *any* tears, but being loved and comforted by Daddy during a transition is a far cry (pardon the pun) from being left in a crib to manage on your own. And it truth, it was more like breaking a habit than weaning from milk in our case.
So, the timing of your question may be fortutous with the upcoming holiday, because that was when we took advantage of hubby's ability to take off of work to "wean" from nap nursing. I had him put her down for the 10 days straight while we were on vacation, and that was that. Then she didn't need it from me. Yes, it took some time and love and patience on Daddy's part, but after a few days it was easier and easier, and then a "new habit" was in place. FYI, she was about 13 or 14 months at that time.
The night nurse we dropped at 18 months, and did it the same way, although we didn't need to time with vacation for that one, just to pick an time where he had no evening work commitments the whole week.
Keep in mind that looking back, I wonder if I should have been so quick to object to being a human pacifier, even if milk had slowed or mostly stopped. Getting her down for nap or sleep was never that easy again! But ultimately, you need to do what is right for you.
Hope this is of some help to you.
Warmly,