Born & raised in Canandaigua NY. Now live in a neighboring town but still work in Canandaigua.
Crime is really low. Very very very safe area.
Cost of living - medium. You will be able to find a safe 3 bedroom house for around $100K in the city of Canandaigua, but you aren't going to get anything spectacular for that. I wouldn't be too optimistic about a nice house with a one acre lot for that price. Maybe an older decent house with quarter acre, or a handyman special with a few acres. You may be able to get something nicer in that price range if you were willing to stretch out into neighboring towns.
Birth & breastfeeding - I've never lived anywhere else so I don't have a comparison. We have one team of midwives that I am aware of that attends home births for this area, and they are beyond wonderful. I would challenge anyone to show me a more wonderful pair of midwives anywhere in the country. I breastfed and never had any issues. I am fairly discreet, like in I cover up with a blanket, but would never go to a bathroom or anything.
Homeschool - My daughter is 2, so I haven't really encountered this yet, but I have looked into it some, and I believe we have a fairly good network available if you include the Rochester area.
Activities - We have a great library in town, they are expanding right now so they are in a temporary location at the moment. This is a beautiful place if you like outdoor activities. We have plenty of parks, the lake, a YMCA (that has homeschool enrichment also.) For culture, Rochester is about 30-40 minutes away and they have plenty of it.
Churches - I'm not a church-going person, so I don't really know. There are a lot of churches around here though so I would have to believe you could find one you like.
Snow - Yup, we get plenty of snow. Figure on a few good storms a year and fairly constant ground cover from December to Early March plus potentially a month on either side in a bad year.