I work in Pawling but am considering living in Wappinger, how bad will my commute be?

It's not terrible but might be a little long. With traffic being a minor issue, I'd say anywhere from a 30-40 minute drive. If you're leaving from Pawling, going across the eastern part of Dutchess County I think you'll be able to get through without a lot of traffic. As you get towards Wappinger, traffic picks up quite a bit during rush hour (coming or going).

The bottom line is that the further away you get from Wappinger, the easier your commute will get, but if traffic poses any issue, you're probably looking at about 40 minutes or so.