I'd take a hard look at the CX or the endurance drop bar bikes. I was in your exact position about 8 months ago. I was looking to do the same type of riding. I rode several different hybrids and ended up with a Giant Escape 3. I'm already eyeing up the Specialized Diverge. I really like the Escape but ride it on the road 75% of the time to try and get in shape. I also ride it on the local rail trails with my wife. My hands were getting tired from one position. I added bar ends and that has helped a lot. But at the end of the day I wish I had started with a drop bar bike. At least now I know what I want! Good luck.