I stopped at an LBS on my way home from work and sat on a couple of bikes. I couldn't ride them (due to the rain at the time), but as I sat on them I wondered -- how will I know if I am too stretched out, or if I just need to get used to that position again? It's been many years since I rode a road bike, so long I can't remember how I felt. I was much younger then and my back and neck were more flexible.
Where is the line between "too much lean", vs. "ideal and my body just needs to adjust"? If I feel like I'm reaching too far, am I really? Or am I just not comfortable with that position yet?