1. I have added fruit in the primary at the tail end of fermentation, or racked onto the fruit in secondary. Both ways work, although there's a lot more sludge to deal with at the end when adding fruit to the primary fermenter. I generally use frozen fruit (or fresh fruit that I froze myself) in my fruit beer, and I've never run into an issue from not sanitizing. I don't know if dried fruit pose any extra risk that fresh/frozen doesn't, but I'd just toss it in. If I was feeling paranoid for one reason or another, then I'd just toss the fruit with some 151 rum or a high-proof bourbon before adding to the beer.
2. I've never run into an issue with stouts carbonating myself, but there's no harm with adding a small amount of dry yeast to each bottle if you want some insurance.
3. I don't think I'd want a stout to be highly carbonated like a champagne, and I would never want a "vigorous secondary fermentation" in a bottle for fear of bottle bombs anyways. I think a low-to-moderate carbonation level (2.2-2.4 volumes of CO2) is best for something like a chocolate cherry stout, so that's what I'd target at bottling if it were me.
You mentioned that you were using dried cherries. Make sure you check to see that no preservatives were added (that may affect fermentation), and you probably don't want it to be sweetened, either.