This is a thought provoking question. My work pattern has been to generally work to complete physical and emotional burn out, and then work more. Then drink. I've got 3 months sober now, and I find that I am less insanely driven than I was before...and I think it's linked to the drinking.
The drinking made me feel a special type of self-loathing that just about made my skin crawl. I felt unworthy, basically all the time. I have always used work to prove my worth. And not so much just with money, but with being in positions of visibility and getting recognition, etc. So, a vicious cycle was set...feel worthless, work harder, faster, more to exhaustion...drink to alleviate the pressure. Drink for a reward, because didn't I earn it after all? Hate myself more. Then work more more more.
Now - I'm finding I'm a bit more laid back. For the first time in my life it's not quite as important to me to be seen as a rock star at work. Of course, I need the money to pay the bills, but the personal strokes and recognition, I care less about. I think maybe it's because I feel more stable and worthy as a person. My self-esteem has definitely increased.
As to your specific question, while you may see the one choice as less stressful, but also less challenging...I think that the lack of challenge may present its own stress. Especially if you have kicked yourself in the past for not stretching yourself. You may wind up feeling that you settled, which may be a trigger in and of itself.
I would look at it this way...life is stressful, period. You can't control everything. You must know in your heart which position you want...forget about your head for a moment. What's your gut telling you? Pick that one...and trust yourself enough to know that you are a strong person who is so much better equipped to make it now than ever before.