I live in Pinellas. I used to work in downtown Clearwater and had another office down in Largo. I used to walk the trail a lot during the day and when I was training for a marathon I was out on most of it between Seminole and Tarpon Springs. I never felt unsafe - but I'm a guy and I was usually on the trail during the day and not evening. There are huge sections of the north part of the trail that would be "safe" but real dark and the trail is a county "linear" park and closed after sunset.
I can see where it would be interesting to go through N. Greenwood on a dark Friday or Saturday evening...