The challenge for me is mainly where we live now and what it affords us. We live in a tiny town of less than 1k people. We're less than 30 mins to work, to kayaking, to great camping, and only a bit further to rock climbing (all the things we both love). There's no crime and taxes are almost entirely non-existent. If either of us were to leave our jobs, there are currently other employers that we could work for and make comparable pay. Together we make far more money than we need and put the large majority of it toward savings and paying off the mortgage. We're on track to have the mortgage paid off by Nov 2019. We're set to be able to retire in about 15 years (well before 62.5/63). We are incredibly fortunate and have worked hard to get where we are.
The challenges in Chi include a few things outside of sacrificing the above. Chicago would be more expensive--we would pay an outrageous amount for housing to live in a place we don't like (sub-$500/mo mortgage for a house vs $2-3k for something comparable). Neither of us have degrees so the opportunities for the wife would likely reduce her income (or mine if I leave the company). Further, I'm not much of a company guy; I don't really care much about getting ahead in a corporate setting. My goals are what will get me the most outdoors time as possible. Living in a city that actively punishes those who try to leave is opposite of what I want long-term.
Now, the reasons I would consider it: if they offered me enough that we could expedite our early retirement while still owning our current house. If they can offer enough, we find a good job for Mrs. Voyage, and we're able to get a good deal on a place, I would consider living there for the next 2-5 years.
Thanks for ringing that bell!