Depends on what time of year. Most of highways are clear of snow and ice, however anything can happen between now and late May.
The roads in that area will be in fair to good condition, if you drive defensively. After the winter we have had on the prairies, potholes and broken sections will probably be evident, however, should be no problem. In that area you will encounter a lot of heavy truck traffic related to the oil boom. We have travelled that area visiting family in Weyburn, and have had no difficulties. All the highways in that area are two lane. If you like to travel off the freeways, and enjoy the slower pace, you will have no problem.