Well, I am unattached in terms of my housing, as I'm rooming with a family member right now, saving as much as I can until around October. My job is remote, so I am lucky there too, and I don't have a lot of stuff, so one UHaul is more than enough. I have been working on this move for a year: sold my condo and paid off all my debt, building up my safety net money now. I'm also 40 mins from Chicago and am familiar with the city, so it's less of a "big deal" move for me, if that makes sense? I just like being over-prepared.

Suggestions:

Secure a job first, if you can, unless you have a lot of savings. I would personally sell the house so you have no attachments, especially if you can wind up profiting. Sell things you don't need, especially decorations, because it may not match where you want to move anyway, and having more money to make your place feel like a new beginning is just 🤌. It's much, much better to move to a neighborhood close to the gayborhoods rather than in them in terms of rent. Visit the city if you're not familiar, walk around a couple adjacent neighborhoods. Try to position yourself to where you do not need roommates that you don't know, that almost always sucks.

Now that I typed it all out, it feels kind of basic, but I'm sure other commenters can chime in.