One of the things that I think we are going to do is rent a trailer for a few weekends this year. Then you can get a feel for if you and your family are going to like it, plus get more comfortable with towing.
It's tough to think about dropping 20K on something to have it sit for 340-350 days out of the year. I think renting is going to give us a better feel for it and i'll be more comfortable if/when we decide to purchase.
http://www.affordablerv.com/rentals.html
http://www.rvdealerscanada.com/rvrentals.php#Alberta