Sorry to hear you're life is in this mess too, as I've said several times, must be something in the water here as there are many IL/Chicago folks on here, Daley must be behind this.
Anyway, although I don't know much of your sitch aside from what is in this thread, you do not sound ready at all for dating. Not even on the "friends with benefits scale". It seems to hold up the letting go cycle. Why do we still hold on to them when we know they don't care, who knows, human nature? As you say, scared of being alone? Fear of rejectment?
I've finally just recently within the past few weeks let go, matter of fact came to full term with it yesterday. Ano now, I am good, I accept it and I LIKE being alone. I'm slowly returning back to the person I used be before my M started to change me into the rollover and say nothing H my W wanted me to be. And you know what, the site, the book(s) can preach all they want about doing 180's and making yourself a better person. Sure it's true, but in the beginning as can be witnessed out of so many threads here, it's only an outside show. While on the inside, we're completely miserable.
Sure the current financial status of everything is scarey all on it's own, but, you know what, I'd be happier living in a cardboard box then having to endure any more of the hurt, misery and pain of still clinging to that last string of hope my STBX will wake up. And truth be told, I probably could have been better, sooner, only I allowed someone to intervine and delay that process. It wasn't anything serious, but enough to distract me from what I needed to do for me.
Sorry to ramble on, but thought I'd share and hopefully something can be learned from my mistake.
Me 35/XW 33 S13 & S12 M: 10/17/98 OM & S: 07/08 D final 06/09/09 12/03/09 - 06/13/10 "Piercing" 06/13/10: Engaged to Re-marry 10/17/10 06/25/10: Expecting baby #3 2/14/11