It is a very good idea to avoid looking in Cleveland during the winter months if at all possible. The availability is so low that your options will feel extremely limited. If you can wait until May to start your apartment search, you will find that you've got ample options to find a suite that matches your requirements nicely.
Take the time to look for a place close to school or work when you're apartment hunting in Cleveland. Although the city is easy enough to navigate, it is large enough that transit times can become problematic if you're hunting in the wrong part of the city.
Wide streets and great signage make Cleveland one of the easiest places to drive in America. As long as you stay off the interstates during the morning and afternoon rush hours, you should find driving in this city much easier than in others of a similar size. You can also hop on the "The Rapid", three train routes that cut across most of the city to connect travelers to the most common destinations and frequently visited neighborhoods in the city.
In sports crazed Cleveland, taking in an Indians, Browns or Cavs game is a great way to get immersed in the kind of fun the locals enjoy. Lake Erie provides ample opportunity for any watersport you could possibly enjoy, including the best fishing of any of the Great Lakes. Downtown Cleveland is a destination within itself. The shopping, dining and drinking available in this region makes it a great place to head to and tour around on foot.