Yes, biking to church can be done with a toddler and a preschooler. See? We go to church about two miles away from where we live, which is highly unusual for the area in which we live. We usually take the car, along with everyone else. But one day the girls were ready to go early, and they also wanted a bike ride. Why not?
So here is one advantage of a sidecar. It may not hold two children, but if you have an older child who is comfortable in on a trailer bike, it doesn't have to. With the sidecar, I can attach the trailer bike; with a trailer bike carrier, I wouldn't be able to.
Yes, biking in a skirt can be tough. Sometimes I wear pants underneath. This particular skirt actually is one of the better ones for the task. I think this was in June.