My partner and I are hoping to qualify for PRP in 2011. We will be doing the Ohio series which is reasonably close to Toronto. You can get more information from the Ohio Randonneurs website at http://www.ohiorand.org/
A great ride for becoming comfortable riding at night is the National 24 Hour Challenge in June in Michigan. It is an UMCA cup event. http://n24hc.org/ The night loop is a 7 mile rectangle (all right turns) with a sheriff at each corner. This is its 28th year so the community knows the cyclists will be on the road all night. And with 350 or so cyclists, you are never alone on the road in the dark. It's a very well organized, fun event.
We ride our 2005 steel Co-Motion Primera Co-Pilot tandem which is heavy but comfortable.