Stuck

So I'm stuck. I am at a total loss as to what to do...things seem to be getting better here, then life rears it's ugly little head and I'm back where I was. Now, things aren't actually all that bad.
1)My friend situation isn't exactly flourishing but maybe I'm getting more ok with that. I spend a lot of time by myself but I tend to like myself better than I like other people so hanging out with me isn't so bad. It would be nice to have a friend to be able to grab a bite to eat or a drink or a movie with...but that doesn't seem to be in the cards for me. It seems as though my friends are a)not speaking to me, b)dating someone and wrapped in that, c)have no money or d)busy. I've tried reaching out to new friends but it seems to go nowhere....So I don't have a plethora of friends here but I've never really had a plethora of friends anywhere....so no big changes there.
2)My living situation is good. I like my apartment. It's a little on the small side but that means less to clean!! In Charleston, I felt like a maid was a necessity...and it kinda was with a 3 bedroom apartment. And cleaning 2.5 baths?? No thanks! Here? Easy peasy. I can get my whole apartment thoroughly cleaned in under an hour.
3) The weather. Oh the weather. Will it ever warm up here? I think the answer is no. I'd like to feel my toes.
4) My job. I like half of it. The other half is filled with a jerkface doctor. I don't know what to do about it. I don't know whether to find a new job and quit. Whether to suck it up and let myself be treated poorly. I just leave there feeling a little more beat down each day. And that's a bad feeling. But finding a new full time job is hard. It would be worth it...but I'm not sure how to go about finding a new job without my current job finding out. The dental community tends to be a small one.

So that brings us to my being stuck. I need to figure out where I want to live after August. Do I want to stay here a little bit longer? Did I really give Chicago enough of a chance? Do I want to move to NC? That's where my roots are and I could be closer to family. Charleston? Or would I end up unhappy there again? It would sure be nice if there were a clear path outlined...
What would you do if you were me?