I hop off the train a stop early on my way home twice a week and pick up my three year old and the bike seat and head out for the last 7.5 miles home. We're good down to forty degrees Fahrenheit. I hate seeing "30% chance of thunderstorms" in the evening forecast on weather.com... it means I have to drive.
We have a trailer, too, but I feel safer with the seat than the trailer.
I just refitted our big cruiser tandem as a sort of longtail with a spare kid seat over the rear wheel and a small BMX seat all the way down for my 5 year old to ride on the back. It doesn't feel so safe, though. But fiddling with it yesterday afternoon served its purpose: getting me to not pull out the credit card and buy the madsen sitting at my LBS.