My husband and I did residency (me) and job (him) at the same time. His job was rare, few places to work and many thought that Feb for a June start was early!
What we did: I applied to 30+ residency spots in the cities where there might be a job. As interview invites came out, we narrowed those down by citiies we were no longer looking at (no job available) and by programs (if 7 in same location and all offered, I chose my favs). Then I canceled some interviews later as well, to make it a manageable number. After all the interviews, I ranked based on my dream (what I want, he follows me), I had him rank my list on his dream (I go where he wants, for job and city to live in) and then I made a reasonable combined list. On rank list day, he had one official offer, one offer pending funding, 2 'no fundings,' so we ranked based on the funded job, then the pending job. We really wnated to stay together but separating for two years or so before he could transfer was also considered.
Maybe you could do soemthing similar? Apply broadly for residency and for med school, knowing that the match gives no choices at the end, and one of you might have to take a "not favorite" or "lower level" to stay together. Also consider if hi residency training will overlap yours once down with med school, and if you should consider your residency options as well? Or just later consider being apart for a year or so, and then consider his options at a fellowship/attending job where you would move to do your residency.
Good luck! It works out if you are both more committed to each other than to your careers- if one is more for the job and one more for each other, there could be resentment done the line.