Orillia Tri/Du

I haven't actually done the brick duathlon but I did train in that area for years while I was in school at UW (both undergrad and gradschool).  I have done the orillia tri twice, but it was a long time ago, so my memory might be a little hazy.  I would say the hills around waterloo are shorter and steeper and the ones around orillia are higher but less steep.  you'll be going up hill for longer, but it isn't too bad.  I'm not a great climber, but I don't recall being completly beat up by the orillia course.  The first 5K is mostly up hill or flat though.  I've always felt sorry for newbies that chose that as their first TAT.

Orillia is a good course - and really great venue.  Funny enough, this is exactly where I did my first Try a Tri.  As to the bike course, it's certainly got some hills in it, but these tend to be quite short but very manageable, even though you will be pushing a smaller gear (be ready for the hill as soon as you leave transition).  The one down side to the bike course is that a few km worth of the road is in rough shape, but overall it's quite good. 

Once you're done the bike, the run is really flat with the exception of one tiny hill (not sure you can even call it that).  I'll be there, and I've had this one marked off as my A race for the year.