Legal Separation & Debt

Location: Wisconsin

I'm starting to prepare a plan for legal separation and/or divorce. We have a son, 5-8 range, 2 cars (in payment), a small home, and roughly 70-90k in marital debt (combined), she has roughly 35k in student loans.

If we go down this road, it's not possible for me to afford a place to live, let alone a 2bd to have joint custody of our son. Child Support and rent before utilities will be over half my monthly income (NET) before any other necessities (meds, car ins, food, utilities, etc).

If we file chapter 7 before separating, I won't be able to rent regardless of having the cash flow.. if I bankrupt after, then I may violate the court ordered debt split (since creditors can seek out her)

I'm working on finding a lawyer to hopefully consult with, and hoping we can do this amicably, but I'm hoping someone has some insight or experiences to share in ways to approach this.

I'm hoping to keep my job and joint custody of our son, I have no desire to keep him from seeing his mom, we just didn't work out (became different people along the 15 yrs).

Another factor is my wife desperately needs to have medical insurance, which makes me lean towards legal separation for the foreseeable future (since my insurance covers spouses who are separated). Her meds without insurance would cost 100s of dollars a month that she just won't have regardless of filing chapter 7. Not having meds isn't an option for her, they are nearly life sustaining.

I'm not concerned about money being tight for me, or having to go without creature comforts, I just need both of us to have custody, and for her to be able to be around for him.

Staying with her is proving to be less of an option week by week for me mentally. So staying together would only compound the issues and bleed over into affecting our son.

I am genuinely fearful that there is no 'good' outcome here..