Just play it by ear. I tried to tandem nurse with each of my other ones, who were about 2 1/2 when I became pg with the next, and it was ok for a few weeks, then nipple pain, then increasingly, I got "the heebies" which was not in my head, but a total physiological sense of revulsion, the need to "get it off! get it off me!" that was really sad to have about my own nursling toddler. For some women, it's mild and goes away. Others don't experience it at all, and for some of us, it gets worse and worse and is unbearable, and becomes good cause to wean. That, and dropping supply.
So don't feel like a terrible Mom if you do end up weaning, and don't feel you have to wean, either. You just won't know til you're there, and it's different for everyone. Hugs! As for trying to gently wean a reluctant toddler, there are discussion groups for that, too, and I hope that helps if you end up heading in that direction. One of mine was easy, and the other two, not!