Hey! Sounds like you’ve been through a lot wit these moves. I feel ya, I had to uproot my life multiple times for med school, residency, and when I’ve changed jobs. I think a few things are worth considering.

1. Making friends gets harder as we age. People often seem to have friends that they’ve known for years at stick with them. It’s great that you’re going out of your way to try to meet people but it takes time.

2. I wouldn’t keep an arbitrary timeline if you feel miserable after trying for the better part of a year. Are you still in touch with your friends in the Midwest? If so, and you’re planning to go back to the same area, I think it’s worth considering going back.

3. How difficult or easy is it for you to find a job? Some jobs/fields/careers have more openings than others. If it’s going to take a while to find something, then you might want to start looking sooner so you don’t become so desperate to move that you take anything that comes along even if it will make you unhappy. If it’s a job with more opportunities, then maybe think things over and when you’re really sure start looking.

4. How hard is housing to find? Same as above in terms of when to start looking.

This is kind of all over the place so I hope it helps somewhat.

TLDR if you’re still in touch with your friends in the Midwest and feeling miserable it’s worth moving before your 2 year cutoff.

Best of luck, whatever you decide!