Here's a legitimate life question I'm pondering.
I work independently in my job like 85% of the time. The other 15% is spent in meetings. I rarely have an impromptu meeting or co-worker "walk-in" happen in my day-to-day. I work/live in Minneapolis. My wife and I really want to move back to central IA to be closer to family and live in a smaller community. I think this can easily be done with my current employer. However, we don't really have any remote employees in the company. At some point, I want to ask my boss about going remote. He seems to really like my work and I really enjoy my job. That being said, if he were to say "no," then I'm likely looking for a new job in order for us to move.
Here's the question: When do I ask my boss? If I ask soon, I could get a "yes" and we start the process of moving. I could also get a "no" and then I'm awkwardly looking for a new job but not really ready to leave my current one; and I will have created a weird dynamic between my boss and I. Or, do I put out feelers about a new job, and then ask about the remote thing so I've already got Plan B, C, and D no matter what his answer is.
I'll hang up and listen.
I had almost the same situation a little over 10 years ago. Myself and my young family at the time had moved to the Minneapolis area for my career, from central Iowa. After about a year up there, while the job was great for me and going well, it was not the right area to be in for my family. So, we began the process to move back to central Iowa. At the time, the company I worked for had no remote program for workers, but were starting to explore the option on a limited basis. With that though, my boss at the time was very old fashioned, for lack of a better term, and not into the whole working remotely thing. So, the way I handled it was that we made preparations to move back to Iowa, I looked for new jobs in the area and once I had an actual job offer on the table back here, I then went to my boss with the work from home question. I was promptly told no and given that I had said that if I can't work remotely I would have to leave the company for a new job, I was told to pack up my things and leave immediately.
So, my advice would be to handle this how you think the boss might react. You might not 100% know, but you probably have a feeling of how they might react to a work from home question. In my case, I knew my boss would have no part of letting me work remotely, so I had plan B ready to go. If I had a more understanding boss, I might have handled it differently. Also, you could feel it out a little, with just asking to work from home from time to time and not bringing up the whole move to Iowa part, at first. If they are willing to let you work from home, where you live now, they might be more open to letting you work from Iowa.