S.T.
Hi L.,
Thank goodness you have a good job. That is a tough situation and you don't want to squash his dream. Maybe you should negotiate something specific with him using the economy as the basis. Have a specific time frame and specific steps he needs to take. I can tell you from a good friend who is a custom home builder that now is not the time to be in that market. He had all sorts of nightmare stories of sub contractors going out of business and more which left him responsible for the repair work.
One other thing I can suggest is tapping him into the ability to consult with attorneys and business consultants. In your message it sounded like if he had access to those resources, maybe some of the bad investments and business decisions might not have happened. Proactive law is always better than reactive. I can tap him into a Home-Base Business Legal plan that would give him unlimited access to attorneys and business consultants (plus some document/contract review benefits, letters written on behalf of the business, plus lots of family benefits including wills, traffic ticket defense, IRS audit support and more) all for a little more than $1 per day.
I think if you get him doing things a little different and having a goal in mind and tapping into helpful resources, you might have a different outcome. However, I think it is reasonable to have a set plan and objectives. Maybe make him do a business plan versus winging it. The services can also give him some insight to that process as well.
Good luck.
S.