Based on my experience trying to get two different cars repaired in the last year, there are a lot of shops looking for mechanics right now...especially anyone with skills (based on my experience at my local dealership, they seem to have a lot of people who have no skills working as mechanics). He should start shopping around now for shops that might be a good fit for him. Side gigs while collecting unemployment can get you into trouble. If your state finds out you were not reporting all income while collecting, they can demand you pay back all unemployment money that you've received. I know this because my husband works in a trade and while he was collecting unemployment, a family member requested some work, so DH did it for free, because he didn't want to jeopardize his unemployment (his family is entitled and probably wouldn't have paid anyway, but it was thousands of dollars worth of free work). 

Sit him down and make him prove his idea will work with numbers and facts.  Make a budget with him.  I swear the only way to get a man to see his ideas in his head are ridiculous is to make him crunch the numbers.  

Not reporting income (and not paying taxes) has negative implications for social security. 

Also, IMHO, it's crappy to do. 

Maybe it is because I am an old guy, this makes no sense to me.

Equity life partners should know it all when it comes to finances.

Sneaky does not work for me in a marriage.

Why is he waiting to be laid off?  Why not get his resume out there right now and start looking for other locations if he’s in such “demand”.   I cannot understand the bass ackwards mentality of I will wait until it’s too late.  Eesh!

I can totallly get where he might have some concern about working for someone he doesn't think has a very good reputation as an employer.

But.. Here are the options he has.

1.  Proactively look for a job and take a job NOW...if he has enough qualifications.. and here is an additional certification an employer might want.. they may even be willing to hire him and send him to school for it.  End result.. he has no gap in employment.

2.  Wait for new owner to take over.. and see how things go.. see if he can work in that organization.. and look later for a new gig if it doesn' pan out well.

3.  Since the company is being bought out.. does it mean the employment of the people goes with it? not sure about how that exactly works.. will everyone be automatically terminated then rehired by the new organization?  (he needs to understand how it would work).

If he elects to not be employed he won't be eligable for unemployment.. and his employer (new/old) will likely fight it because it does cost them money for him to file.  

If he quits and works side jobs.. and files and gets unemployment.. he could be found to have defrauded the state and could be subject to severe penalties.

If he quits and works side jobs and is denied unemployement.. he may not have enough to pay his bills.

It seems the smart thing is to dust off his resume and interview skills and see what options are out there.  Clearly his current employer is on the way out.. one way or another.  Unemployment is unlikely to be an option.. and as you saw.. he will not make much from it.. probably not enough to cover what he owes for his joint and CS obligations.  I get that he is freshly seeing this as a problem now.. that leaving a long term employer was not in his plans.. and it's scary to think about new stuff.  But.. at this point.. the writing is on the wall.. he needs to proceed in a way that will protect you both.. that means not engaging in FRAUD.. and not quitting when he has an option of staying and working for mr doodoo head.. even if that's not what he wants.. at least it pays the bills and he can be looking for a job now.. and ongoing so working for mr jerky pants should be short lived hopefully.

The option he likely does NOT have is asking to be laid off.. it just usually doesn't work out that way.

He needs to research how unemployment works. It costs the company when someone goes on unemployment - they pay for unemployment insurance. Since the company will be changing hands, the existing owners and/or the new owners may not want to go along with this "plan." An employer can fight an employees request for unemployment.

In most states, you have to prove you are looking for work in order to stay on unemployment. Given the need for workers and your husbands skill set, he would have to lie on the forms because he could get a job. You can't stay on unemployment forever - that differs by state as well.

This plan is not well thought out from a financial or moral aspect. I know you have been struggling with some of his choices when it comes to how his actions effect your marriage - and this seems like another huge problem.

What's the chance that he would STAY unemployed?  Is that your true worry,  that he would run with the "great idea" of his and become dead weight you carry?  As if you haven't done enough for him already, putting up with all the drama from his baggage.  I would not offer much in financial support and insist that he carry his own financial weight during this job transition.  You can't blame all of the SDs problems on BM, they have their father as a role model also.  

You are always in a much stronger position when looking for jobs when you are still in full-time employment. You have negotiating power. Once you are unemployed, you no longer have that advantage. 

The best time to get a better job is while you're employed. Fact. Give his age, he'll probably have to work a bit harder to find a good one. Also fact.

I think this is one of those times when your H's history with addiction is showing. He's not making logical decisions and panicking a bit. Side jobs, seriously? He might as well join the circus.

In this, you're the grownup. I second the idea of putting together a spreadsheet of expenses and going over the budget with him, then guiding him in his job search. Be calm and emphasize he could find a better job for better pay in this market. And if he wants to be a baby, tell him he can sell the big boat to meet expenses. That should make him straighten up.

My DH had a situation where the facility he worked for was bought by a new company. He didn't want to work for them. He looked in a rush and got a different job. I was supportive of that. It's not uncommon for people look for a new job in situations of mergers or ownership switch 

DH also was in a situation where he was unable to return to the employment after surgery because surgeon wouldn't give him a permission out of a fear of re-injury so he had to hurry up and look for a new job. I was supportive if there had to be a gap in employment in case he can't get a job fast enough (was no gap, he got the job quickly), and I was supportive if he had to take reasonable pay cut as his health is more important (ended up actually pay increase not cut).

id also support my DH if at some point his job becomes way too much for him health wise and he might have to stay in the field but in a less demanding and less pay position. The time will likely come and I'll support that. We are way into our 50s. second half. Not getting younger 

Having said that I'd not support anything illegal or stupid. Just because he's my husband it doesn't mean I must be dutiful wife supporting idiocy. Asking for being laid off (no one lays off upon request), collecting unemployment while doing side gigs (it's illegal and dumb). Hhhmm no. Nothing what he proposed sounds even remotely appropriate or wise. He better rethink it ASAP. 

Now because the job openings are about to dry up.  The domino effect lay offs have begun.

As doing 10 hours of work in 8 hours by beating book time .?    Any place would love a person who can beat book time  ,,,more money for repair place. ,,,More money for worker.   
Secong thought, can he buy the busines ?   Work sometimes out. So much down so much per month for X number of years.  Nobody can get a business load, the old owners will have to hold the note no matter who buy it. Unless national chane