Bumping this since it's a 7 year old thread and I'm preparing to take Eliana out and about soon!
We took Miguel everywhere in the trailer. Since we (and you) already have decent knowledge of good routes in general, you have a solid base to work from. Riding-with-trailer skill is more important than route selection. Some trailer tips are here. http://bikewinter.org/kids
People might honk and yell at you for "endangering" your child, but if they are yelling, that means they see you. No one* wants to hit someone, esp someone carrying a child.
Start with low stake trips (ie, ones where you don't have to be somewhere at a certain time) and have someone ride behind you to give you feedback on your roadway positioning. You need to get used to having a slightly "wider load" ie less clearance.
You need to take corners a little more carefully 1) to make sure you are visible and have enough clearance and 2) so you don't hit a curb cut which can lead to the trailer tipping
Just pretend you are driving a flatbed truck and make lots of eye contact. :) Good luck!
*Well, almost no one and anyone that does transcends questions of biking set up. I posted this in another forum recently, but it is relevant.