I'll emphasize that I'm not in great shape (finished hiking the AT a year ago, have pretty much been sitting in front of a computer screen ever since) . Also, I prefer trail-running to roads/sidewalks or flat park areas.
My suggestion is Occoneechee Mountain in Hillsborough as that'll provide some nice ups and downs, but we can mix it up for variety. Anyone else interested? Even just one nice long jog a week would be nice, though I'd be up for trying more frequent runs.