Every now and then I see on a bike shop's website that they will have last year's version of the same model of another bike, but it's marked down by a few hundred dollars. Unfortunately, from what I've seen these are usually pretty few and far between. Is there a good place to look that has a good selection of outdated bikes (preferably road bikes)?
Here in the Toronto area, you can find these bikes either at a spring bike show or (more commonly) fall bike show. They are generally priced aggressively to clear out stock and you won't find many in the stores in the coming years.
Most shops will not have previous model years around as they make money selling bikes and want to move stock.
I also managed to find my girl's bike on Kijiji the same way that a shop just wanted to clear out last years model. 40% off.
The final option is a few bike stores that sit on stock for years and they won't move on the price regardless and you won't convince them.
Bike shops from one area to the next can be as different as oranges and orangutans. The same can be true of bike shops within a given area.
Here in the "Olympia Washington Metroplex", there are seven bike shops: Deschutes (on Custer), Deschutes (on 4th), Joy Ride, Old Town, Bike Tech, Falcones, REI
There are a couple of different bike collectives: Evergreen College Bike Shop, Build A Bike, Intercity Transit's program (which is aimed at kids).
There are also a couple of bike builders here in town, but that's probably off topic from what you want.
Falcones, I'm told, can be a good place to find previous year's models still sitting in boxes--sometimes bikes from 10 or more years ago. I got a previous year's model for my son at REI 2 years ago, and I've seen previous year's models for sale at most of the local shops. Deschutes specializes in used bikes and upgrades, so they are my shop of choice.
Some of this information might be found online at BikeForums, Yelp, etc. However, the best way to find it out is by visiting the local shops. Go to Google Maps, enter "bike shops in " without the quotes. Check out their hours, make a day of it, and visit them all. Go in without any plan to buy. Just visit, see what they've got, get a feel for the place. Some places might rub you wrong. Others might feel like they were put there to serve you.