Congrats on getting into running. I've been running fun runs and longer races for about 10 years now. My favorite run is Crazy Legs in Madison. It is run through the campus and ends on the 50 yard line at Camp Randall. The race is 5 miles and usually is the last weekend in April. I also competed in the mens health urbanathalon in Chicago this last October. What a blast. 10 miles with some ridiculous obstacles mixed in the course (1 mile of the run was running stairs at soldier field). Check out the website for the course description. I have bad knees and have always had trouble with shoes. In May I started using the nike free v.3. It is considered a barefoot style running shoe and is the greatest thing I have invested in. I can run longer and more comfortably than ever before and have noticed that my ankles are stronger than they used to be. It took a couple weeks of running with them to get used to the feel but now I can't run in normal shoes. They sell them in v. 3, 5, 7 with the 3 being the closest to barefoot and each level adding more support as you go up. I have a pair of the 5's but they aren't as comfortable to me as the 3's. Hope this helps.