He is very motivated for change and I feel like we're so close to finding a solution, if we can just get the moving parts to click into place.
There is no magic "click" of all the moving parts neatly clicking into place.
The answer is for "him" to make a complete list of all debt owed - totals, interest, due dates - assess the potential for negotiation of due dates, interest rates, terms, etc.
Split by business and personal.
Can he currently afford the minimum payments on all his monthly bills?
A spreadsheet or a written list will tell him - there is no magic trick, this will be a long slog to settle and deal with. Does he have skills and work options, can he earn side income? That is all worth a discussion - as mustachians might see clearly what you both may not. Like you are hoping for a solution, there may well be different options/radical alternatives to tackle some of this debt.
A consolidation loan is generally nothing but an easy way out and statistically speaking most people end up in the same position again. Apparently, having to deal with the painful consequences of your past actions yourself on a monthly basis has a "financially" healing effect.
Nothing motivates one more than pain - there is a reason we say debt is crushing.
If you want some fresh eyes and good ideas - ask this question in the "Ask a mustachian" thread ... but only after he has done his home work and can present us with all the numbers and a complete picture of his financial obligations.
There are plenty of people here with enormous soul-crushing debt who've dealt with their situation or are still working on it - especially in the journals. He has to find his own way and do it in a way that makes sense to him so he can commit to a pay-off plan and find a way out of this mess. Unless he is a super earner it will take years, so you re-visit and re-evaluate your plans as you go and you find that eventually, things ease up a bit.
He isn't the only person with a failed business or money troubles. We live - we learn - we move on.
Congrats to you for paying off your own debt. I am pleased to see you want to help him, but speaking as an old lady with tons of life experience, I say, "This is his mess to fix". Nothing wrong with lending your support. You may well make the difference for him to be able to find his way out of this financial stranglehold.