This is all great feedback. We have rentals out of town, so I'm not too worried about renters and we would certainly look for a good investment. We have a pretty good idea where we want to land, but we might not be as clear on the details (condo? SF? In the city? outside of the city?) Just renting when we get to that point is a great idea.
Personally, as I think about this journey, I find my mind jumping to the end. Maybe the question behind the question is finding that balance between working the day to day plan but considering how to make a transition to something different.
Thanks again for the feedback.