I am originally from North Battleford Saskatchewan and now live in Calgary, Alberta.
I know there are kite groups in both Regina and Saskatoon. There are also dealers in both those places so you may be able to test equipment. But the kiting scene is somewhat small so the dealers may not have much equipment in stock.
As for a kite I suggest a large inflatable with lots of depower. So a bow or Supported leading edge kite at least 13m. I found that often the winds on the praries are not overly strong and it is very rare that the wind goes above where you can hold down a 13.
If you want to spend more money a 16 and a 11 would be good together. You don't want a 16 as your only kite because they are just far too large and are more difficult to ride and learn on.
Get a real kiteboard do not use a wakeboard and make sure it is a twintip. I assume you don't wakeboard so you will want a beginner board Liquid force drop is supposed to be good and won't kill your wallet.
You may be interested in some kites that are on sale from a dealer here in Calgary.
They have 2006 Ozone Instincts for $500 (canadian).
They are demo kites but are in great condition and at that price you can't go wrong. I own an Instinct 13 and have rode in 60kph winds. The people are very friendly and it is a nice mom and pop organization.
Other useful hints:
-Find a lake in your area with a large beach or a large grassy area next to the water. It is also great if there is a shallow bay so that you can ride on smooth water.
-In the winter. It is all about the frozen lakes.
-Get a wetsuit. A 3/4 shorty will work and you can probably start riding in early to mid June.
-Stick close to shore. Learning results in crashes and failed relaunches and swimming in sucks.
-Buy a teaching dvd even if you take lessons. Lessons should be taken if available but the dvd will give you pointers that you can learn and see work then apply to your riding. You will get much more out of the lessons this way.
-Since you are new to kites buy a trainer right now. And fly it as often as possible until the water warms up. This will teach you to fly the kites. Make sure to crash that trainer and twist it and try to sort the mess out. Kites are easy to work with when everything is going well but you need to be able to recover from a real screw up. Once you get your big kite learn how the bar works, how the safeties work, and how to set it up.
-Do not fly it on land
unless the wind is so light that it will barely take off. And if you do fly it, which you may not be able to resist doing, the area must be very big and open. Since your in good ole SK drive out of town find a field that is not seeded, preferable ask the farm if you can go out on the empty land (they usually don't care as long as you are not breaking things), and set up there. Where you will have tons of space.
Hope all that helps.